Chapter 5 Oligosaccharide Synthesis: From Conventional Methods to Modern Expeditious Strategies

Advances in Carbohydrate Chemistry and Biochemistry

Volumn 62, Issue , 2009, Pages 161-250

  Smoot, James T ^a   Demchenko, Alexei V ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

Carbohydrates; Glycoconjugates; Glycosylation; Oligosaccharides; Synthetic strategy

Indexed keywords

GLYCOSIDASE; GLYCOSYLTRANSFERASE; HYDROLASE; OLIGOSACCHARIDE; POLYMER; ENZYME;

ANALYTIC METHOD; CHEMICAL ANALYSIS; GLYCOSYLATION; HIGH THROUGHPUT SCREENING; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTOR; REVIEW; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; CARBOHYDRATE ANALYSIS; CHEMISTRY; ENZYME SPECIFICITY; METABOLISM; MOLECULAR GENETICS; STEREOISOMERISM; TIME;

CARBOHYDRATE SEQUENCE; ENZYMES; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TIME FACTORS;

EID: 66249093859     PISSN: 00652318     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2318(09)00005-5     Document Type: Review

References (290)

1. Nicolaou K.C., and Ueno H. Oligosaccharide synthesis from glycosyl fluorides and sulfides. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, Inc., New York 313-338
2. Fraser-Reid B., Wu Z., Udodong U.E., and Ottosson H. Armed/disarmed effects in glycosyl donors: rationalization and sidetracking. J. Org. Chem. 55 (1990) 6068-6070
3. Williams L.J., Garbaccio R.M., and Danishefsky S.J. Iterative assembly of glycals and glycal derivatives: The synthesis of glycosylated natural products and complex oligosaccharides. In: Ernst B., Hart G.W., and Sinay P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 61-92
4. Kanie O., Ito Y., and Ogawa T. Orthogonal glycosylation strategy in oligosaccharide synthesis. J. Am. Chem. Soc. 116 (1994) 12073-12074
5. Ito Y., Kanie O., and Ogawa T. Orthogonal glycosylation strategy for rapid assembly of oligosaccharides on a polymer support. Angew Chem. Int. Ed. 35 (1996) 2510-2512
6. Roy R., Andersson F.O., and Letellier M. "Active" and "latent" thioglycosyl donors in oligosaccharide synthesis. Application to the synthesis of α-sialosides. Tetrahedron Lett. 33 (1992) 6053-6056
7. Boons G.-J., and Isles S. Vinyl glycosides in oligosaccharide synthesis. Part 1: A new latent-active glycosylation strategy. Tetrahedron Lett. 35 (1994) 3593-3596
8. Douglas N.L., Ley S.V., Lucking U., and Warriner S.L. Tuning glycoside reactivity: New tool for efficient oligosaccharides synthesis. J. Chem. Soc., Perkin Trans. 1 (1998) 51-65
9. Zhang Z., Ollmann I.R., Ye X.S., Wischnat R., Baasov T., and Wong C.-H. Programmable one-pot oligosaccharide synthesis. J. Am. Chem. Soc. 121 (1999) 734-753
10. Ye X.S., and Wong C.-H. Anomeric reactivity-based one-pot oligosaccharide synthesis: A rapid route to oligosaccharide libraries. J. Org. Chem. 65 (2000) 2410-2431
11. Green L.G., and Ley S.V. Protecting groups: Effects on reactivity, glycosylation specificity and coupling efficiency. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 427-448
12. Bilodeau M.T., Park T.K., Hu S., Randolph J.T., Danishefsky S.J., Livingston P.O., and Zhang S. Total synthesis of a human breast tumor associated antigen. J. Am. Chem. Soc. 117 (1995) 7840-7841
13. Lassaletta J., and Schmidt R.R. Glycosyl imidates. Part 75. Synthesis of the hexasaccharide moiety of globo H (human breast cancer) antigen. Liebigs Ann. (1996) 1417-1423
14. Zhu T., and Boons G.-J. A two-directional and highly convergent approach for the synthesis of the tumor-associated antigen Globo-H. Angew. Chem., Int. Ed. Engl. 38 (1999) 3495-3497
15. Burkhart F., Zhang A., Wacowich-Sgarbi S., and Wong C.-H. Synthesis of the globo H hexasaccharide using the programmable reactivity-based one-pot strategy. Angew. Chem. Int. Ed. 40 (2001) 1274-1277
16. Bosse F., Marcaurelle L.A., and Seeberger P.H. Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3. J. Org. Chem. 67 (2002) 6659-6670
17. Huang L., Wang Z., and Huang X. One-pot oligosaccharide synthesis: Reactivity tuning by post-synthetic modification of aglycone. Chem. Commun. (2004) 1960-1961
18. Huang X., Huang L., Wang H., and Ye X.S. Iterative one-pot synthesis of oligosaccharides. Angew Chem., Int. Ed. 43 (2004) 5221-5224
19. Wang Z., Zhou L., Ei-Boubbou K., Ye X.S., and Huang X. Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors. J. Org. Chem. 72 (2007) 6409-6420
20. Codée J.D.C., Litjens R.E.J.N., van den Bos L.J., Overkleeft H.S., and van der Marel G.A. Thioglycosides in sequential glycosylation strategies. Chem. Soc. Rev. 34 (2005) 769-782
21. Crich D. Chemistry of glycosyl triflates: Synthesis of β-mannopyranosides. J. Carbohydr. Chem. 21 (2002) 667-690 (reprinted from
22. Glycochemistry: Principles, Synthesis, and Applications (2001) 53-75
23. Gin D. Dehydrative glycosylation with 1-hydroxy donors. J. Carbohydr. Chem. 21 (2002) 645-665 (reprinted from
24. Glycochemistry: Principles, Synthesis, and Applications (2001) 33-52
25. Plante O.J., Palmacci E.R., and Seeberger P.H. Automated solid-phase synthesis of oligosaccharides. Science 291 (2001) 1523-1527
26. Seeberger P.H. Automated carbohydrate synthesis to drive chemical glycomics. Chem. Commun. (2003) 115-1121
27. Lowary T.L. d-Arabinofuranosides from mycobacteria: Synthesis and conformation. J. Carbohydr. Chem. 21 (2002) 691-722 (reprinted from
28. Glycochemistry: Principles, Synthesis, and Applications (2001) 133-162
29. Lam S.N., and Gervay-Hague J. Solution- and solid-phase oligosaccharide synthesis using glucosyl iodides: A comparative study. Carbohydr. Res. 337 (2002) 1953-1965
30. Hadd M.J., and Gervay J. Glycosyl iodides are highly efficient donors under neutral conditions. Carbohydr. Res. 320 (1999) 61-69
31. Wang C.C., Lee J.C., Luo S.Y., Fan H.F., Pai C.L., Yang W.C., Lu L.D., and Hung S.-C. Synthesis of biologically potent α1 → 2-linked disaccharide derivatives via regioselective one-pot protection-glycosylation. Angew. Chem. Int. Ed. 41 (2002) 2360-2362
32. Wang C.C., Lee J.C., Luo S.Y., Kulkarni S.S., Huang Y.W., Lee C.C., Chang K.L., and Hung S.-C. Regioselective one-pot protection of carbohydrates. Nature 446 (2007) 896-899
33. Kim J.H., Yang H., Park J., and Boons G.-J. A general strategy for stereoselective glycosylations. J. Am. Chem. Soc. 127 (2005) 12090
34. Kim J.H., Yang H., and Boons G.-J. Stereoselective glycosylation reactions with chiral auxiliaries. Angew. Chem. Int. Ed. 44 (2005) 947-949
35. Boons G.-J. Strategies in oligosaccharide synthesis. Tetrahedron 52 (1996) 1095-1121
36. Kanie O. Orthogonal strategy in oligosaccharide synthesis. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 407-426
37. Koeller K.M., and Wong C.-H. Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies. Chem. Rev. 100 (2000) 4465-4493
38. Davis B.G. Recent developments in oligosaccharide synthesis. J. Chem. Soc., Perkin Trans. 1 (2000) 2137-2160
39. Kanemitsu T., and Kanie O. Recent developments in oligosaccharide synthesis: Tactics, solid-pase synthesis and library synthesis. Comb. Chem. High Throughput Screen. 5 (2002) 339-360
40. Demchenko A.V. Strategic approach to the chemical synthesis of oligosaccharides. Lett. Org. Chem. 2 (2005) 580-589
41. Wang Y., Ye X.S., and Zhang L.H. Oligosaccharide assembly by one-pot multi-step strategy. Org. Biomol. Chem. 5 (2007) 2189-2200
42. In: Demchenko A.V. (Ed). Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance (2008), Wiley-VCH, Weinheim
43. Kunz H., and Schultz M. Glycopeptide synthesis in solution and on the solid phase. In: Ernst B., Hart G.W., and Sinay P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 267-304
44. Hang H.C., and Bertozzi C.R. Chemoselective approaches to glycoprotein assembly. Acc. Chem. Res. 34 (2001) 727-736
45. Koeller K.M., and Wong C.-H. Glycoproteins: Synthesis and applications of biologically relevant glycopeptides. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology Vol. 3 (2001), Springer, Berlin 2305-2352
46. Davis B.G. Synthesis of glycoproteins. Chem. Rev. 102 (2002) 579-601
47. Marcaurelle L.A., and Bertozzi C.R. Mini review recent advances in the chemical synthesis of mucin-like glycoproteins. Glycobiology 12 (2002) 69R-77R
48. Pratt M.R., and Bertozzi C.R. Synthetic glycopeptides and glycoproteins as tools for biology. Chem. Soc. Rev. 34 (2005) 58-68
49. Kahne D., Leimkuhler C., Lu W., and Walsh C. Glycopeptide and lipoglycopeptide antibiotics. Chem. Rev. 105 (2005) 425-448
50. Tvaroška I., and Bleha T. Anomeric and exo-anomeric effects in carbohydrate chemistry. Adv. Carbohydr. Chem. Biochem. 47 (1989) 45-123
51. Goodman L. Neighboring-group participation in sugars. Adv. Carbohydr. Chem. Biochem. 22 (1967) 109-175
52. Nukada T., Bérces A., Zgierski M.Z., and Whitfield D.M. Exploring the mechanism of neighboring group assisted glycosylation reactions. J. Am. Chem. Soc. 120 (1998) 13291-13295
53. Toshima K., and Tatsuta K. Recent progress in O-glycosylation methods and its application to natural-products synthesis. Chem. Rev. 93 (1993) 1503-1531
54. Nitz M., and Bundle D.R. Oligosaccharides: Synthesis: Glycosyl halides in oligosaccharide synthesis. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology Vol. 2 (2001), Springer, Berlin 1497-1542
55. Igarashi K. The Koenigs-Knorr reaction. Adv. Carbohydr. Chem. Biochem. 34 (1977) 243-283
56. Schmidt R.R., and Jung K.H. Trichloroacetimidates. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 5-59
57. Mukaiyama T. Explorations into new reaction chemistry. Angew. Chem. Int. Ed. 43 (2004) 5590-5614
58. Garegg P.J. Thioglycosides as glycosyl donors in oligosaccharide synthesis. Adv. Carbohydr. Chem. Biochem. 52 (1997) 179-205
59. Oscarson S. Thioglycosides. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 93-116
60. Fraser-Reid B., and Madsen R. Oligosaccharide synthesis by n-pentenyl glycosides. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, Inc., New York 339
61. Fraser-Reid B., Anilkumar G., Gilbert M.B., Joshi S., and Kraehmer R. Glycosylation methods: Use of n-pentenyl glycosides. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 135-154
62. Lu J., and Fraser-Reid B. Preparation, properties, and applications of n-pentenyl arabinofuranosyl donors. Org. Lett. 6 (2004) 3051-3054
63. van den Bos L.J., Dinkelaar J., Overkleeft H.S., and van der Marel G.A. Stereocontrolled synthesis of β-d-mannuronic acid esters: synthesis of an alginate trisaccharide. J. Am. Chem. Soc. 128 (2006) 13066-13067
64. Hanashima S., Castagner B., Esposito D., Nokami T., and Seeberger P.H. Synthesis of a sialic acid α(2-3) galactose building block and Its use in a linear synthesis of sialyl Lewis X. Org. Lett. 9 (2007) 1777-1779
65. Ishiwata A., Munemura Y., and Ito Y. Synergistic solvent effect in 1,2-cis-glycosides formation. Tetrahedron 64 (2008) 92-102
66. Slaghek T.M., van Oijen A.H., Maas A.A.M., Kamerling J.P., and Vliegenthart J.F.G. Synthesis of structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B. Carbohydr. Res. 207 (1990) 237-248
67. Love K.R., Andrade R.B., and Seeberger P.H. Linear synthesis of a protected h-type II pentasaccharide using glycosyl phosphate building blocks. J. Org. Chem. 66 (2001) 8165-8176
68. Koto S., Uchida T., and Zen S. Syntheses of isomaltose, isomaltotetraose, and isomaltooctaose. Bull. Chem. Soc. Jpn. 46 (1973) 2520-2523
69. Paulsen H. Advances in selective chemical syntheses of complex oligosaccharides. Angew. Chem. Int. Edit. Engl. 21 (1982) 155-173
70. Ogawa T., Yamamoto H., Nukada T., Kitajima T., and Sugimoto M. Synthetic approach to glycan chains of a glycoprotein and proteoglycan. Pure Appl. Chem. 56 (1984) 779-795
71. Gu G., and Du Y. Synthesis of a pentasaccharide derivative corresponding to a triterpenoid saponin isolated from Spergularia ramosa. J. Chem. Soc., Perkin Trans. 1 (2002) 2075-2079
72. Depre D., Düffels A., Green L.G., Lenz R., Ley S.V., and Wong C.-H. Synthesis of glycans from the glycodelins: Two undeca-, two deca-, three nona-, an octa- and a heptasaccharide. Chem. Eur. J. 5 (1999) 3326-3340
73. Matsuo I., Totani K., Tatami A., and Ito Y. Comprehensive synthesis of ER related high-mannose-type sugar chains by convergent strategy. Tetrahedron 62 (2006) 8262-8277
74. x antigen. Liebigs Ann. Chem. (1991) 425-433
75. Sundgren A., Lahmann M., and Oscarson S. Block synthesis of Streptococcus pneumoniae type 14 capsular polysaccharide structures. J. Carbohydr. Chem. 24 (2005) 379-391
76. a sequence. J. Carbohydr. Chem. 17 (1998) 647-672
77. Mukaiyama T., Ikegai K., Jona H., Hashihayata T., and Takeuchi K. A convergent total synthesis of the mucin related F1a antigen by one-pot sequential stereoselective glycosylation. Chem. Lett. (2001) 840-841
78. Chowdhury A.R., Siriwardena A., and Boons G.-J. A highly convergent approach for the synthesis of disaccharide repeating units of peptidoglycan. Tetrahedron Lett. 43 (2002) 7805-7807
79. Backinowsky L.V., Abronina P.I., Shashkov A.S., Grachev A.A., Kochetkov N.K., Nepogodiev S.A., and Stoddart J.F. An efficient approach towards the convergent synthesis of "fully-carbohydrate" mannodendrimers. Chem. Eur. J. 8 (2002) 4412-4423
80. Dudkin V.Y., Miller J.S., and Danishefsky S.J. A concise route to the core pentasaccharide of N-linked glycoproteins. Tetrahedron Lett. 44 (2003) 1791-1793
81. Xue J., and Guo Z. Convergent synthesis of a GPI containing an acylated inositol. J. Am. Chem. Soc. 125 (2003) 16334-16339
82. Warren J.D., Miller J.S., Keding S.J., and Danishefsky S.J. Toward fully synthetic glycoproteins by ultimately convergent routes: A solution to a long-standing problem. J. Am. Chem. Soc. 126 (2004) 6576-6578
83. Liu X., Kwon Y.U., and Seeberger P.H. Convergent synthesis of a fully lipidated glycosylphosphatidylinositol anchor of Plasmodium falciparum. J. Am. Chem. Soc. 127 (2005) 5004-5005
84. Fraser-Reid B., Lu J., Jayaprakash K.N., and Lopez J.C. Synthesis of a 28-mer oligosaccharide core of mycobacterial lipoarabinomannan (LAM) requires only two n-pentenyl orthoester progenitors. Tetrahedron Asymmetry 17 (2006) 2449-2463
85. Crich D., Wu B., and Jayalath P. Convergent synthesis of a β-(1→3)-mannohexaose. J. Org. Chem. 72 (2007) 6806-6815
86. Gening M.L., Tsvetkov Y.E., Pier G.B., and Nifantiev N.E. Synthesis of β-(1→6)-linked glucosamine oligosaccharides corresponding to fragments of the bacterial surface polysaccharide poly-N-acetylglucosamine. Carbohydr. Res. 342 (2007) 567-575
87. Rao Y., and Boons G.-J. A highly convergent chemical synthesis of conformational epitopes of rhamnogalactan II. Angew. Chem. Int. Ed. 46 (2007) 6148-6151
88. Joe M., Bai Y., Nacario R.C., and Lowary T.L. Synthesis of the docosanasaccharide arabinan domain of mycobacterial arabinogalactan and a proposed octadecasaccharide biosynthetic precursor. J. Am. Chem. Soc. 129 (2007) 9885-9901
89. Jayaprakash K.N., Chaudhuri S.R., Murty C.V.S.R., and Fraser-Reid B. Regioselective strategies mediated by lanthanide triflates for efficient assembly of oligomannans. J. Org. Chem. 72 (2007) 5534-5545
90. Cheon H.S., Lian Y., and Kishi Y. Highly stereoselective and iterative synthesis of α-(1→4)-linked polysaccharides composed of 3-O-methyl-d-mannose. Org. Lett. 9 (2007) 3323-3326
91. Manabe S., Ishii K., and Ito Y. Synthesis of a natural oligosaccharide antibiotic active against Helicobacter pylori. J. Org. Chem. 72 (2007) 6107-6115
92. Oberli M.A., Bindschadler P., Werz D.B., and Seeberger P.H. Synthesis of a hexasaccharide repeating unit from Bacillus anthracis vegetative cell wall. Org. Lett. 10 (2008) 905-908
93. Deng K., Adams M.M., and Gin D.Y. Synthesis and structure verification of the vaccine adjuvant QS-7-Api. Synthetic access to homogeneous Quillaja saponaria immunostimulants. J. Am. Chem. Soc. 130 (2008) 5860-5861
94. Nicolaou K.C., Dolle R.E., Papahatjis D.P., and Randall J.L. Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a. J. Am. Chem. Soc. 106 (1984) 4189-4192
95. Randall J.L., and Nicolaou K.C. Preparation and reactions of glycosyl fluorides. ACS Symp. Ser. 374 (1988) 13-28
96. Lönn H. Synthesis of a tri- and a heptasaccharide which contain α-l-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins. Carbohydr. Res. 139 (1985) 105-113
97. Lönn H. Synthesis of a tetra- and a nona-saccharide which contain α-l-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins. Carbohydr. Res. 139 (1985) 115-121
98. Garegg P.J., and Oscarson S. A synthesis of 8-methoxycarbonyloct-1-yl O-α-d-galactopyranosyl-(1→3)-O-β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside. Carbohydr. Res. 136 (1985) 207-213
99. Fügedi P., Garegg P.J., Lonn H., and Norberg T. Thioglycosides as glycosylating agents in oligosaccharide synthesis. Glycoconjugate J. 4 (1987) 97-108
100. Leontein K., Nilsson M., and Norberg T. Synthesis of the methyl and 1-octyl glycosides of the P-antigen tetrasaccharide (globotetraose). Carbohydr. Res. 144 (1985) 231-240
101. Paulsen H., Heume M., and Nurnberger H. Synthese der verzwiegten Nonasaccharid-Sequenz der "bisected" Structur von N-Glycoproteinen. Carbohydr. Res. 200 (1990) 127-166
102. Ziegler T., Eckhardt E., and Birault V. Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens. J. Org. Chem. 58 (1993) 1090-1099
103. Yamada H., Harada T., and Takahashi T. Synthesis of an elicitor-active hexaglucoside analogue by a one-pot, two-step glycosidation procedure. J. Am. Chem. Soc. 116 (1994) 7919-7920
104. Aoki S., Kondo H., and Wong C.-H. Glycosyl phosphites as glycosylation reagents. Methods Enzymol. 247 (1994) 193-211
105. Plante O.J., Palmacci E.R., Andrade R.B., and Seeberger P.H. Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents. J. Am. Chem. Soc. 123 (2001) 9545-9554
106. Demchenko A.V., Malysheva N.N., and De Meo C. S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation. Org. Lett. 5 (2003) 455-458
107. Demchenko A.V., Kamat M.N., and De Meo C. S-Benzoxazolyl (SBox) glycosides in oligosaccharide synthesis: novel glycosylation approach to the synthesis of β-d-glucosides, β-d-galactosides, and α-d-mannosides. Synlett (2003) 1287-1290
108. Demchenko A.V., Pornsuriyasak P., De Meo C., and Malysheva N.N. Potent, versatile, and stable: thiazolyl thioglycosides as glycosyl donors. Angew. Chem., Int. Ed. 43 (2004) 3069-3072
109. Pornsuriyasak P., and Demchenko A.V. Glycosyl thioimidates in a highly convergent one-pot strategy for oligosaccharide synthesis. Tetrahedron Asymmetry 16 (2005) 433-439
110. Kochetkov N.K., Malysheva N.N., Klimov E.M., and Demchenko A.V. Synthesis of polysaccharides with 1,2-cis-glycosidic linkages by trityl-thiocyanate polycondensation-stereoregular α-(1→6)-d-glucan. Tetrahedron Lett. 33 (1992) 381-384
111. Klimov E.M., Malysheva N.N., Demchenko A.V., and Kochetkov N.K. Synthesis of 1,2-cis-linked regular heteropolysaccharide - rhamnoglucan. Dokl. Akad. Nauk 330 (1993) 331-332
112. Codée J.D.C., van den Bos L.J., Litjens R.E.J.N., Overkleeft H.S., van Boom J.H., and van der Marel G.A. Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors. Org. Lett. 5 (2003) 1947-1950
113. 2O: A powerful promotor system in chemoselective glycosylations using thioglycosides. Org. Lett. 5 (2003) 1519-1522
114. Raghavan S., and Kahne D. A one-step synthesis of ciclamycin trisaccharide. J. Am. Chem. Soc. 115 (1993) 1580-1581
115. Yan L., Taylor C.M., Goodnow R., and Kahne D. Glycosylation on the Merrifield resin using anomeric sulfoxides. J. Am. Chem. Soc. 116 (1994) 6953-6954
116. Mehta S., and Pinto B.M. Phenylselenoglycosides as novel, versatile glycosyl donors. selective activation over thioglycosides. Tetrahedron Lett. 32 (1991) 4435-4438
117. Mehta S., and Pinto B.M. Novel glycosidation methodology. The use of phenylselenoglycosides as glycosyl donors and acceptors in oligosaccharide synthesis. J. Org. Chem. 58 (1993) 3269-3276
118. Zuurmond H.M., van der Meer P.H., van der Klein P.A.M., van der Marel G.A., and van Boom J.H. Iodonium-promoted glycosylations with phenyl selenoglycosides. J. Carbohydr. Chem. 12 (1993) 1091-1103
119. Baeschlin D.K., Chaperon A.R., Charbonneau V., Green L.G., Ley S.V., Lucking U., and Walther E. Rapid assembly of oligosaccharides: Total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei. Angew. Chem. Int. Edit. 37 (1998) 3423-3428
120. Fraser-Reid B., Udodong U.E., Wu Z.F., Ottosson H., Merritt J.R., Rao C.S., Roberts C., and Madsen R. n-Pentenyl glycosides in organic chemistry: A contemporary example of serendipity. Synlett (1992) 927-942 and references therein
121. Demchenko A., and Boons G.-J. A highly convergent synthesis of a hexasaccharide derived from the oligosaccharide of group B type III Streptococcus. Tetrahedron Lett. 38 (1997) 1629-1632
122. Demchenko A.V., and Boons G.-J. A highly convergent synthesis of a complex oligosaccharide derived from group B type III Streptococcus. J. Org. Chem. 66 (2001) 2547-2554
123. Hanessian S., Huynh H.K., Reddy G.V., Duthaler R.O., Katopodis A., Streiff M.B., Kinzy W., and Oehrlein R. Synthesis of Gal determinant epitopes, their glycomimetic variants, and trimeric clusters-relevance to tumor associated antigens and to discordant xenografts. Tetrahedron 57 (2001) 3281-3290
124. Lou B., Reddy G.V., Wang H., and Hanessian S. Glycoside and oligosaccharide synthesis with unprotected glycosyl donors based on the remote activation concept. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, Inc., New York 389
125. Lou B., Eckhardt E., and Hanessian S. Oligosaccharide synthesis by selective anomeric activation with MOP- and TOPCAT-leaving groups. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, Inc., New York 449
126. Kiso M., and Anderson L. Protected glycosides and disaccharides of 2-amino-2-deoxy-d-glucopyranose by ferric chloride-catalyzed coupling. Carbohydr. Res. 136 (1985) 309-323
127. Fügedi P., Garegg P.J., Oscarson S., Rosen G., and Silvanis B.A. Glycosyl 1-piperidinecarbodithioates in the synthesis of glycosides. Carbohydr. Res. 211 (1991) 157-162
128. Marra A., Gauffeny F., and Sinaÿ P. A novel class of glycosyl donors: anomeric S-xanthates of 2-azido-2-deoxy-d-galactopyranosyl derivatives. Tetrahedron 47 (1991) 5149-5160
129. Chenault H.K., and Castro A. Glycosyl transfer by isopropenyl glycosides: Trisaccharide synthesis in one pot by selective coupling of isopropenyl and n-pentenyl glycopyranosides. Tetrahedron Lett. 35 (1994) 9145-9148
130. Stick R.V., Tilbrook D.M.G., and Williams S.J. The selective activation of telluro- over seleno- β-d-glucopyranosides as glycosyl donors: A reactivity scale for various telluro, seleno and thio sugars. Aust. J. Chem. 50 (1997) 237-240
131. Takeuchi K., Tamura T., and Mukaiyama T. The trityl tetrakis(pentafluorophenyl)borate catalyzed stereoselective glycosylation using new glycosyldonor, 3,4,6-tri-O-benzyl-2-O-p-toluoyl-β-d-glucopyranosyl phenylcarbonate. Chem. Lett. (2000) 122-123
132. Bogusiak J., and Szeja W. Block synthesis of oligosaccharides. Part 1: Preparation of furanosyl-1-thiopyranosides. Tetrahedron Lett. 42 (2001) 2221-2223
133. Codée J.D.C., Stubba B., Schiattarella M., Overkleeft H.S., van Boeckel C.A.A., van Boom J.H., and van der Marel G.A. A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy. J. Am. Chem. Soc. 127 (2005) 3767-3773
134. Garcia B.A., Poole J.L., and Gin D.Y. Direct glycosylations with 1-hydroxy glycosyl donors using trifluoromethanesulfonic anhydride and diphenyl sulfoxide. J. Am. Chem. Soc. 119 (1997) 7597-7598
135. Crich D., and Smith M. 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages. J. Am. Chem. Soc. 123 (2001) 9015-9020
136. 3, a ganglioside. Chem. Lett. (1996) 337-338
137. 3. J. Carbohydr. Chem. 15 (1996) 857-878
138. Kamat M.N., De Meo C., and Demchenko A.V. S-Benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis. J. Org. Chem. 72 (2007) 6947-6955
139. 3). J. Am. Chem. Soc. 110 (1988) 7910-7912
140. Yamago S., Yamada T., Hara O., Ito H., Mino Y., and Yoshida J. A new, iterative strategy of oligosaccharide synthesis based on highly reactive β-bromoglycosides derived from selenoglycosides. Org. Lett. 3 (2001) 3867-3870
141. Halcomb R.L., and Danishefsky S.J. On the direct epoxidation of glycals: Application of a reiterative strategy for the synthesis of β-linked oligosaccharides. J. Am. Chem. Soc. 111 (1989) 6661-6666
142. Danishefsky S.J., and Bilodeau M.T. Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence. Angew. Chem. Int. Ed. Engl. 35 (1996) 1380-1419
143. Deshpande P.P., Kim H.M., Zatorski A., Park T.K., Ragupathi G., Livingston P.O., Live D., and Danishefsky S.J. Strategy in oligosaccharide synthesis: An application to a concise total synthesis of the KH-1(adenocarcinoma) antigen. J. Am. Chem. Soc. 120 (1998) 1600-1614
144. Murray R.W., and Jeyaraman R. Dioxiranes: synthesis and reactions of methyldioxiranes. J. Org. Chem. 50 (1985) 2847-2853
145. Randolph J.T., McClure K.F., and Danishefsky S.J. Major simplifications in oligosaccharide syntheses arising from a solid-phase based method: An application to the synthesis of the Lewis b antigen. J. Am. Chem. Soc. 117 (1995) 5712-5719
146. 4-Mediated transformation of n-pentenyl glycosides to glycosyl fluorides: A new pair of semiorthogonal glycosyl donors. Org. Lett. 9 (2007) 2759-2762
147. Cao S., Hernandez-Mateo F., and Roy R. Scope and applications of "active and latent" thioglycosyl donors. Part 4. J. Carbohydr. Chem. 17 (1998) 609-631
148. Rodebaugh R., Debenham J.S., Fraser-Reid B., and Snyder J.P. Bromination of alkenyl glycosides with copper (II) bromide and lithium bromide: synthesis, mechanism, and DFT calculations. J. Org. Chem. 64 (1999) 1758-1761
149. Allen J.G., and Fraser-Reid B. n-Pentenyl glycosyl orthoesters as versatile intermediates in oligosaccharide synthesis. The proteoglycan linkage region. J. Am. Chem. Soc. 121 (1999) 468-469
150. Wang P.G., Haldar P., Wang Y., and Hu H. Simple glycosylation reaction of allyl glycosides. J. Org. Chem. 72 (2007) 5870-5873
151. Kim K.S., Kim J.H., Lee Y.J., Lee Y.J., and Park J. 2-(Hydroxycarbonyl)benzyl glycosides: A novel type of glycosyl donors for highly efficient β-mannopyranosylation and oligosaccharide synthesis by latent-active glycosylation. J. Am. Chem. Soc. 123 (2001) 8477-8481
152. Hinklin R.J., and Kiessling L.L. Glycosyl sulfonylcarbamates: New glycosyl donor with tunable reactivity. J. Am. Chem. Soc. 123 (2001) 3379-3380
153. Paulsen H. Progress in oligosaccharide synthesis through a new orthogonal glycosylation strategy. Angew. Chem. Int. Ed. Engl. 34 (1995) 1432-1434
154. Kanie O., Ito Y., and Ogawa T. Orthogonal glycosylation strategy in synthesis of extended blood group B determinant. Tetrahedron Lett. 37 (1996) 4551-4554
155. Kanie O., Ohtsuka I., Ako T., Daikoku S., Kanie Y., and Kato R. Orthogonal glycosylation reactions on solid phase and synthesis of a library consisting of a complete set of fucosyl galactose isomers. Angew Chem. Int. Ed. 45 (2006) 3851-3854
156. Pornsuriyasak P., and Demchenko A.V. S-Thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis. Chem. Eur. J. 12 (2006) 6630-6646
157. S. Kaeothip, P. Pornsuriyasak, N. P. Rath, and A. V. Demchenko, Unexpected orthogonality of the S-benzoxazolyl and S-thiazolinyl derivatives: Application to expeditious oligosaccharide assembly. Org. Lett., 11 (2009) 799-802.
158. Demchenko A.V., and De Meo C. semi-Orthogonality of O-pentenyl and S-ethyl glycosides: Application for the oligosaccharide synthesis. Tetrahedron Lett. 43 (2002) 8819-8822
159. Boons G.-J., Geurtsen R., and Holmes D. Chemoselective glycosylations (Part 1): Differences in size of anomeric leaving groups can be exploited in chemoselective glycosylations. Tetrahedron Lett. 36 (1995) 6325-6328
160. Geurtsen R., Cote F., Hahn M.G., and Boons G.-J. Chemoselective glycosylation strategy for the convergent assembly of phytoalexin-elicitor active oligosaccharides and their photoreactive derivatives. J. Org. Chem. 64 (1999) 7828-7835
161. Pornsuriyasak P., Gangadharmath U.B., Rath N.P., and Demchenko A.V. A novel strategy for oligosaccharide synthesis via temporarily deactivated S-thiazolyl glycosides as glycosyl acceptors. Org. Lett. 6 (2004) 4515-4518
162. Pornsuriyasak P., Rath N.P., and Demchenko A.V. 4-(Pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation. Chem. Commun (2008) 5633-5635
163. Lahmann M., and Oscarson S. One-pot oligosaccharide synthesis exploiting solvent reactivity effects. Org. Lett. 2 (2000) 3881-3882
164. Mootoo D.R., Konradsson P., Udodong U.E., and Fraser-Reid B. "Armed" and "disarmed" n-pentenyl glycosides in saccharide couplings leading to oligosaccharides. J. Am. Chem. Soc. 110 (1988) 5583-5584
165. Konradsson P., Mootoo D.R., McDevitt R.E., and Fraser-Reid B. Iodonium ion generated in situ from N-iodosuccinimide and trifluoromethanesulphonic acid promotes direct linkage of "disarmed" pent-4-enyl glycosides. J. Chem. Soc., Chem. Commun. (1990) 270-272
166. Ratcliffe A.J., Konradsson P., and Fraser-Reid B. n-Pentenyl glycosides as efficient synthons for promoter-mediated assembly of N-α-linked glycoproteins. J. Am. Chem. Soc. 112 (1990) 5665-5667 and references therein
167. Veeneman G.H., and van Boom J.H. An efficient thioglycoside-mediated formation of a-glycosidic linkages promoted by iodonium dicollidine perchlorate. Tetrahedron Lett. 31 (1990) 275-278
168. Barrena M.I., Echarri R., and Castillón S. Synthesis of disaccharides by selective metallocene promoted activation of glycosyl fluorides. Synlett (1996) 675-676
169. Hashimoto S.I., Sakamoto H., Honda T., Abe H., Nakamura S.I., and Ikegami S. "Armed-disarmed" glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: a convergent synthesis of globotriaosylceramide. Tetrahedron Lett. 38 (1997) 8969-8972
170. Chiba H., Funasaka S., Kiyota K., and Mukaiyama T. Catalytic and chemoselective glycosylation between armed and disarmed glycosyl p-trifluoromethylbenzylthio-p-trifluoromethylphenyl formimidates. Chem. Lett. (2002) 746-747
171. Friesen R.W., and Danishefsky S.J. On the controlled oxidative coupling of glycals: A new strategy for the rapid assembly of oligosaccharides. J. Am. Chem. Soc. 111 (1989) 6656-6660
172. Kamat M.N., and Demchenko A.V. Revisiting the armed-disarmed concept rationale: Chemoselective activation of the S-benzoxazolyl glycosides in oligosaccharide synthesis. Org. Lett. 7 (2005) 3215-3218
173. Smoot J.T., Pornsuriyasak P., and Demchenko A.V. Development of an arming participating group for stereoselective glycosylation and chemoselective oligosaccharide synthesis. Angew. Chem. Int. Ed. 44 (2005) 7123-7126
174. Fraser-Reid B., Wu Z., Andrews C.W., and Skowronski E. Torsional effects in glycoside reactivity: Saccharide couplings mediated by acetal protecting groups. J. Am. Chem. Soc. 113 (1991) 1434-1435
175. Wilson B.G., and Fraser-Reid B. n-Pentenyl glycoside based methodology for determining the relative reactivities of variously protected pairs of glycosides. J. Org. Chem. 60 (1995) 317-320
176. Fridman M., Solomon D., Yogev S., and Baasov T. One-pot synthesis of glucosamine oligosaccharides. Org. Lett. 4 (2002) 281-283
177. Clausen M.H., and Madsen R. Synthesis of hexasaccharide fragments of pectin. Chem. Eur. J. 9 (2003) 3821-3832
178. Schmidt T., and Madsen R. Glycosylations directed by the armed-disarmed effect with acceptors containing a single ester group. Eur. J. Org. Chem. 2007 (2007) 3935-3941
179. Crich D., and Li M. Revisiting the armed-disarmed concept: The importance of anomeric configuration in the activation of S-benzoxazolyl glycosides. Org. Lett. 9 (2007) 4115-4118
180. Boons G.-J., Grice P., Leslie R., Ley S.V., and Yeung L.L. Dispiroketals in synthesis (Part 5): A new opportunity for oligosaccharide synthesis using differentially activated glycosyl donors and acceptors. Tetrahedron Lett. 34 (1993) 8523-8526
181. Baeschlin D.K., Chaperon A.R., Green L.G., Hahn M.G., Ince S.J., and Ley S.V. 1,2-Diacetals in synthesis: Total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei. Chem. Eur. J. 6 (2000) 172-186
182. Zhu T., and Boons G.-J. Thioglycosides protected as Trans-2,3-cyclic carbonates in chemoselective glycosylations. Org. Lett. 3 (2001) 4201-4203
183. Jensen H.H., Nordstrom L.U., and Bols M. The disarming effect of the 4,6-acetal group on glycoside reactivity: Torsional or electronic?. J. Am. Chem. Soc. 126 (2004) 9205-9213
184. Pedersen C.M., Nordstrom L.U., and Bols M. "Super armed" glycosyl donors: Conformational arming of thioglycosides by silylation. J. Am. Chem. Soc. 129 (2007) 9222-9235
185. Jensen H.H., Pedersen C.M., and Bols M. Going to extremes: "Super" armed glycosyl donors in glycosylation chemistry. Chem. Eur. J. 13 (2007) 7576-7582
186. Mydock L.K., and Demchenko A.V. Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection. Org. Lett. 10 (2008) 2103-2106
187. Mydock L.K., and Demchenko A.V. Application of the superarmed glycosyl donor to chemoselective oligosaccharide synthesis. Org. Lett. 10 (2008) 2107-2110
188. Fraser-Reid B., Lopez J.C., Radhakrishnan K.V., Nandakumar M.V., Gomez A.M., and Uriel C. One pot/two donors/one diol give one differentiated trisaccharide: Powerful evidence for reciprocal donor-acceptor selectivity (RDAS). Chem. Commun. (2002) 2104-2105
189. Adachi M., Tanaka H., and Takahashi T. An effective sialylation method using N-Troc and N-Fmoc-protected β-thiophenyl sialosides and application to the one-pot two-step synthesis of 2,6-sialyl-T antigen. Synlett (2004) 609-614
190. Jayaprakash K.N., and Fraser-Reid B. One-pot chemo-, regio-, and stereoselective double-differential glycosidation mediated by lanthanide triflates. Org. Lett. 6 (2004) 4211-4214
191. Rising T.W.D.F., Heidecke C.D., and Fairbanks A.J. Synlett (2007) 1421-1425
192. Eller S., Schuberth R., Gundel G., Seifert J., and Unverzagt C. Synthesis of pentaantennary N-glycans with bisecting GlcNAc and core fucose. Angew. Chem. Int. Ed. 46 (2007) 4173-4175
193. Unverzagt C., Eller S., Mezzato S., and Schuberth R. A double regio- and stereoselective glycosylation strategy for the synthesis of N-glycans. Chem. Eur. J. 14 (2008) 1304-1311
194. Tanaka H., Adachi M., Tsukamoto H., Ikeda T., Yamada H., and Takahashi T. Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks. Org. Lett. 4 (2002) 4213-4216
195. y). Tetrahedron Lett. 35 (1994) 7927-7930
196. Anilkumar G., Nair L.G., and Fraser-Reid B. Targeted glycosyl donor delivery for site-selective glycosylation. Org. Lett. 2 (2000) 2587-2589
197. Uriel C., Gomez A.M., Lopez J.C., and Fraser-Reid B. Further insight into 'matching' of donors and acceptors via reciprocal donor acceptor selectivity (RDAS) studies. Synlett (2003) 2203-2207
198. Du Y., Gu G., Wei G., Hua Y., and Linhardt R.J. Synthesis of saponins using partially protected glycosyl donors. Org. Lett. 5 (2003) 3627-3630
199. Gu G., Du Y., and Linhardt R.J. Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors. J. Org. Chem. 69 (2004) 5497-5500
200. Boons G.-J., and Demchenko A.V. Recent advances in O-sialylation. Chem. Rev. 100 (2000) 4539-4565
201. Danishefsky S.J., and Allen J.R. From the laboratory to the clinic: A retrospective on fully synthetic carbohydrate-based anticancer vaccines. Angew. Chem. Int. Ed. 39 (2000) 836-863
202. Wang Z.G., and Hindsgaul O. Combinatorial carbohydrate chemistry. In: Axford (Ed). Glycoimmunology 2 (1998), Plenum Press, New York 219-236
203. Boons G.-J. Combinatorial approaches in oligosaccharide synthesis. Carbohydr. Eur. (1999) 28-32
204. Schweizer F., and Hindsgaul O. Combinatorial synthesis of carbohydrates. Curr. Opin. Chem. Biol. 3 (1999) 291-298
205. Fukase K. Oligosaccharides: Synthesis: Combinatorial and solid phase methods in oligosaccharide synthesis. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology Vol. 2 (2001), Springer, Berlin 1621-1660
206. Garegg P.J., Maloisel J.L., and Oscarson S. Stannylene activation in glycoside synthesis: Regioselective glycosidations at the primary position of galactopyranosides unprotected in the 2-,3-,4-, and 6-positions. Synthesis (1995) 409-414
207. Oshima K., and Aoyama Y. Regiospecific glycosidation of unprotected sugars via arylboronic activation. J. Am. Chem. Soc. 121 (1999) 2315-2316
208. Lopez J.C., Agocs A., Uriel C., Gomez A.M., and Fraser-Reid B. Iterative, orthogonal strategy for oligosaccharide synthesis based on the regioselective glycosylation of polyol acceptors with partially unprotected n-pentenyl-orthoesters: further evidence for reciprocal donor acceptor selectivity (RDAS). Chem. Commun. (2005) 5088-5090
209. Tsvetkov Y.E., Kitov P.I., Backinowsky L.V., and Kochetkov N.K. Unusual regioselective glycosylation of sugar secondary trityloxy function in the presence of primary one. Tetrahedron Lett. 34 (1993) 7977-7980
210. Tsvetkov Y.E., Kitov P.I., Backinowsky L.V., and Kochetkov N.K. Highly regioselective glycosylation of a secondary position in sugar primary-secondary ditrityl ethers. J. Carbohydr. Chem. 15 (1996) 1027-1050
211. Boons G.-J., and Zhu T. Novel regioselective glycosylations for the convergent and chemoselective assembly of oligosaccharides. Synlett (1997) 809-811
212. Zhu T., and Boons G.-J. Two-directional, convergent synthesis of a pentasaccharide that is involved in the hyperacute rejection response in xenotransplantation from pig to man. J. Chem. Soc., Perkin Trans. 1 (1998) 857-862
213. Zhu T., and Boons G.-J. A two directional glycosylation strategy for the convergent assembly of oligosaccharides. Tetrahedron Lett. 39 (1998) 2187-2190
214. Boons G.-J., Bowers S., and Coe D.M. Trityl ethers in oligosaccharide synthesis: A novel strategy for the convergent assembly of oligosaccharides. Tetrahedron Lett. 38 (1997) 3773-3776
215. Zhu T., and Boons G.-J. A two-directional approach for the solid-phase synthesis of trisaccharide libraries. Angew. Chem. Int. Ed. 37 (1998) 1898-1900
216. Grice P., Ley S.V., Pietruszka J., Priepke H.W.M., and Walther E.P.E. Tuning the reactivity of glycosides: efficient one-pot oligosaccharide synthesis. Synlett (1995) 781-784
217. Mong T.K.-K., and Wong C.-H. Reactivity-based one-pot synthesis of a Lewis Y carbohydrate hapten: a colon-rectal cancer antigen determinant. Angew. Chem. Int. Ed. 41 (2002) 4087-4090
218. Mong T.K.-K., Huang C.-Y., and Wong C.-H. A new reactivity-based one-pot synthesis of N-acetyllactosamine oligomers. J. Org. Chem. 68 (2003) 2135-2142
219. Mong T.K.-K., Lee H.-K., Duron S.G., and Wong C.-H. Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: A sialylated antigenic epitope of small-cell lung cancer. Proc. Nat. Acad. Sci. USA 100 (2003) 797-802
220. Lee J.C., Wu C.Y., Apon J.V., Siuzdak G., and Wong C.-H. Reactivity-based one-pot synthesis of the tumor-associated antigen N3 minor octasaccharide for the development of a photocleavable DIOS-MS sugar array. Angew. Chem. Int. Ed. 45 (2006) 2753-2757
221. Polat T., and Wong C.-H. Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides. J. Am. Chem. Soc. 129 (2007) 12795-12800
222. Baeschlin D.K., Green L.G., Hahn M.G., Hinzen B., Ince S.J., and Ley S.V. Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides. Tetrahedron Asymmetry 11 (2000) 173-197
223. Valverde S., Garcia M., Gomez A.M., and Lopez J.C. A combined intramolecular-intermolecular one-pot glycosylation approach for the synthesis of a branched trisaccharide. Chem. Commun. (2000) 813-814
224. Hiroshi T., Matoba N., and Takahashi T. Effective one-pot synthesis of H type 1 and 2 trisaccharide derivatives using glycal epoxide. Chem. Lett. 34 (2005) 400-401
225. Bhattacharyya S., Magnusson B.G., Wellmar U., and Nilsson U.J. The p-methoxybenzyl ether as an in situ -removable carbohydrate-protecting group: a simple one-pot synthesis of the globotetraose tetrasaccharide. J. Chem. Soc. Perkin Trans. 1 8 (2001) 886-890
226. Winter M. Support for solid-phase organic synthesis. In: Jung G. (Ed). Combinatorial Peptide and Nonpeptide Libraries (1996), VCH, Weinheim 465-510
227. Fruchtel J.S., and Jung G. Organic chemistry on solid supports. Angew. Chem. Int. Ed. Engl. 35 (1996) 17-42
228. Hermkens P.H.H., Ottenheijm H.C.J., and Rees D. Solid-phase organic reactions: A review of the recent literature. Tetrahedron 52 (1996) 4527-4554
229. Brown R.C.D. Recent developments in solid-phase organic synthesis. J. Chem. Soc., Perkin Trans. 1 (1998) 3293-3320
230. Osborn H.M.I., and Khan T.H. Recent developments in polymer supported syntheses of oligosaccharides and glycopeptides. Tetrahedron 55 (1999) 1807-1850
231. Krepinsky J.J., and Douglas S.P. Polymer-supported synthesis of oligosaccharides. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 239-265
232. Seeberger P.H., and Haase W.C. Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries. Chem. Rev. 100 (2000) 4349-4393
233. Seeberger P.H. Solid phase oligosaccharide synthesis. J. Carbohydr. Chem. 21 (2002) 613-643 (reprinted from
234. Glycochemistry: Principles, synthesis, and applications (2001) 1-32
235. Ando H., Manabe S., Nakahara Y., and Ito Y. Tag-reporter strategy for facile oligosaccharide synthesis on polymer support. J. Am. Chem. Soc. 123 (2001) 3848-3849
236. Sears P., and Wong C.-H. Toward automated synthesis of oligosaccharides and glycoproteins. Science 291 (2001) 2344-2350
237. Crich D., and Smith M. Solid-phase synthesis of β-mannosides. J. Am. Chem. Soc. 124 (2002) 8867-8869
238. Manabe S., and Ito Y. On-resin real-time reaction monitoring of solid-phase oligosaccharide synthesis. J. Am. Chem. Soc. 124 (2002) 12638-12639
239. Majumdar D., Zhu T., and Boons G.-J. Synthesis of oligosaccharides on soluble high-molecular-weight branched polymers in combination with purification by nanofiltration. Org. Lett. 5 (2003) 3591-3594
240. Ojeda R., de Paz J.L., and Martin-Lomas M. Synthesis of heparin-like oligosaccharides on a soluble polymer support. Chem. Commun. (2003) 2486-2487
241. Ojeda R., Terenti O., de Paz J.L., and Martin-Lomas M. Synthesis of heparin-like oligosaccharides on polymer supports. Glycoconjugate J. 21 (2004) 179-195
242. Wu X., and Schmidt R.R. Solid-phase synthesis of complex oligosaccharides using a novel capping reagent. J. Org. Chem. 69 (2004) 1853-1857
243. Bauer J., and Rademann J. Hydrophobically assisted switching phase synthesis: The flexible combination of solid-phase and solution-phase reactions employed for oligosaccharide preparation. J. Am. Chem. Soc. 127 (2005) 7296-7297
244. Dondoni A., Marra A., and Massi A. Hybrid solution/solid-phase synthesis of oligosaccharides by using trichloroacetyl isocyanate as sequestration-enabling reagent of sugar alcohols. Angew. Chem. Int. Ed. 44 (2005) 1672-1676
245. Hanashima S., Manabe S., and Ito Y. Divergent synthesis of sialylated glycan chains: Combined use of polymer support, resin capture-release, and chemoenzymatic strategies. Angew Chem. Int. Ed. 44 (2005) 4218-4228
246. Ako T., Daikoku S., Ohtsuka I., Kato R., and Kanie O. A method of orthogonal oligosaccharide synthesis leading to a combinatorial library based on stationary solid-phase reaction. Chem. Asian J. 1 (2006) 798-813
247. Jonke S., Liu K.-g., and Schmidt R.R. Solid-phase oligosaccharide synthesis of a small library of N-glycans. Chem. Eur. J. 12 (2006) 1274-1290
248. Branderhorst H.A., Liskamp R.A.J., and Pieters R.J. Solid-phase carbohydrate synthesis via on-bead protecting group chemistry. Tetrahedron 63 (2007) 4290-4296
249. Doi T., Kinbara A., Inoue H., and Takahashi T. Donor-bound glycosylation for various glycosyl acceptors: Bidirectional solid-phase semisynthesis of vancomycin and its derivatives. Chem. Asian J. 2 (2007) 188-198
250. Plante O.J., Palmacci E.R., and Seeberger P.H. Development of an automated oligosaccharide synthesizer. Adv. Carbohydr. Chem. Biochem. 58 (2003) 35-54
251. x oligosaccharide on polymeric support. J. Am. Chem. Soc. 122 (2000) 10222-10223
252. Ferguson J., and Marzabadi C. On-resin generation and reactions of orthogonal glycosyl donors. Tetrahedron Lett. 44 (2003) 3573-3577
253. Parlato M.C., Kamat M.N., Wang H., Stine K.J., and Demchenko A.V. Application of glycosyl thioimidates in polymer-supported oligosaccharide synthesis. J. Org. Chem. 73 (2008) 1716-1725
254. Wu X., Grathwohl M., and Schmidt R.R. Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: Use of a novel linker and temporary-protecting-group pattern. Angew. Chem. Int. Ed. 41 (2002) 4489-4493
255. Seeberger P.H., and Werz D.B. Automated synthesis of oligosacchraides as a basis for drug discovery. Nat. Rev. 4 (2005) 751-763
256. Seeberger P.H., and Werz D.B. Synthesis and medical applications of oligosaccharides. Nature 446 (2007) 1046-1051
257. Seeberger P.H. Automated oligosaccharide synthesis. Chem. Soc. Rev. 37 (2008) 19-28
258. Hewitt M.C., Snyder D.A., and Seeberger P.H. Rapid synthesis of a glycosylphosphatidylinositol-based malaria vaccine using automated solid-phase oligosaccharide synthesis. J. Am. Chem. Soc. 124 (2002) 13434-13436
259. Werz D.B., Castagner B., and Seeberger P.H. Automated synthesis of the tumor-associated carbohydrate antigens Gb-3 and Globo-H: Incorporation of α-galactosidic linkages. J. Am. Chem. Soc. 129 (2007) 2770-2771
260. Miura T., Goto K., Waragai H., Matsumoto H., Hirose Y., Ohmae M., Ishida H., Satoh A., and Inazu T. Rapid oligosaccharide synthesis using a fluorous protective group. J. Org. Chem. 69 (2004) 5348-5353
261. Ratner D.M., Murphy E.R., Jhunjhunwala M., Snyder D.A., Jensen K.F., and Seeberger P.H. Microreactor-based reaction optimization in organic chemistry - glycosylation as a challenge. Chem. Comm. (2005) 578-580
262. Carrel F.R., Geyer K., Codée J.D.C., and Seeberger P.H. Oligosaccharide synthesis in microreactors. Org. Lett. 9 (2007) 2285-2288
263. Pathlak A.K., Yerneni C.K., Young Z., and Pathlak V. Oligomannan synthesis using ionic liquid supported glycosylation. Org. Lett. 10 (2008) 145-148
264. Wong C.-H., Halcomb R.L., Ichikawa Y., and Kajimoto T. Enzymes in organic synthesis: Application to the problems of carbohydrate recognition (part 1). Angew. Chem., Int. Ed. Engl. 34 (1995) 412-432
265. Wong C.-H., Halcomb R.L., Ichikawa Y., and Kajimoto T. Enzymes in organic synthesis: Application to the problems of carbohydrate recognition (part 2). Angew. Chem., Int. Ed. Engl. 34 (1995) 521-546
266. Kirby A.J. Enzyme mechanisms, models, and mimics. Angew. Chem., Int. Ed. Engl. 35 (1996) 707-724
267. David S., Augé C., and Gautheron C. Enzymic methods in preparative carbohydrate chemistry. Adv. Carbohydr. Chem. Biochem. 49 (1991) 175-237
268. Kren V., and Thiem J. Glycosylation employing bio-systems: From enzymes to whole cells. Chem. Soc. Rev. 26 (1997) 463-473
269. Hehre E.J. Glycosyl transfer: a history of the concept's development and view of its major contributions to biochemistry. Carbohydr. Res. 331 (2001) 347-368
270. Gambert U., and Thiem J. Chemical transformations employing glycosyltransferases. Topics Curr. Chem. 186 (1997) 21-43
271. van den Eijnden D.H. On the origin of oligosaccharide species - glycosyltransferases in action. In: Ernst B., Hart G.W., and Sinay P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 589-624
272. Renkonen O. Enzymatic glycosylations with glycosyltransferases. In: Ernst B., Hart G.W., and Sinay P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 647-662
273. Augé C., Le Narvor C., and Lubineau A. Solid-phase synthesis with glycosyltransferases. In: Ernst B., Hart G.W., and Sinay P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 705-722
274. Qian X., Sujino K., Otter A., Palcic M.M., and Hindsgaul O. Chemoenzymatic synthesis of α-(1- > 3)-Gal(NAc)-terminating glycosides of complex tertiary sugar alcohols. J. Am. Chem. Soc. 121 (1999) 12063-12072
275. Qian X., Sujino K., and Palcic M.M. Enzymatic glycosylations with non-natural donors and acceptors. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 685-704
276. Sujino K., Uchiyama T., Hindsgaul O., Seto N.O.L., Wakarchuk W.W., and Palcic M.M. Enzymatic synthesis of oligosaccharide analogues: evaluation of UDP-Gal analogues as donors for three retaining α-galactosyltransferases. J. Am. Chem. Soc. 122 (2000) 1261-1269
277. Ohrlein R. Synthesis of sugar nucleotides. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 625-646
278. Koeller K.M., and Wong C.-H. Recycling of sugar nucleotides in enzymatic glycosylation. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 663-684
279. Yu H., Chokhawala H., Karpel R., Yu H., Wu B., Zhang J., Zhang Y., Jia Q., and Chen X. A multifunctional Pasteurella multocida sialyltransferase: A powerful tool for the synthesis of sialoside libraries. J. Am. Chem. Soc. 127 (2005) 17618-17619
280. Yi W., Shao J., Zhu L., Li M., Lu Y., Lin S., Li H., Ryu K., Shen J., Guo H., Yao Q., Bush C.A., and Wang P.G. E. coli O86 O-antigen biosynthetic gene cluster and stepwise enzymatic synthesis of human blood group B antigen tetrasaccharide. J. Am. Chem. Soc. 127 (2005) 2040-2041
281. Tachibana Y., Takaha T., Fujiwara S., Takagi M., and Imanaka T. Acceptor specificity of 4-α-glucanotransferase from Pyrococcus kodakaraensis KOD1, and synthesis of cycloamylose. J. Biosci. Bioeng. 90 (2000) 406-409
282. Scigelova M., Singh S., and Crout D.H.G. Glycosidases - a great synthetic tool. J. Mol. Catal. B-Enzym. 6 (1999) 483-494
283. Vocadlo D.J., and Withers S.G. Glycosidase-catalyzed oligosaccharide synthesis. In: Ernst B., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley-VCH, Weinheim 723-844
284. Hehre E.J. A fresh understanding of the stereochemical behavior of glycosylases: Structural distinction of "inverting" (2-MCO-type) versus "retaining" (1-MCO-type) enzymes. Adv. Carbohydr. Chem. Biochem. 55 (2000) 265-310
285. Vic G., Hastings J.J., and Crout D.H.G. Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: Application to the chemoenzymatic synthesis of galactopyranosyl-(1→4)-O-α-galactopyranoside derivatives. Tetrahedron Asymmetry 7 (1996) 1973-1984
286. Nilsson K.G.I. A simple strategy for changing the regioselectivity of glycosidase-catalyzed formation of disaccharides. Carbohydr. Res. 167 (1987) 95-103
287. Singh S., Scigelova M., and Crout D.H.G. Glycosidase-catalysed synthesis of α-galactosyl epitopes important in xenotransplantation and toxin binding using the α-galactosidase from Penicillium multicolor. Chem. Commun. (1999) 2065-2066
288. Dion M., Nisole A., Spangenberg P., Andre C., Glottin-Fleury A., Mattes R., Tellier C., and Rabiller C. Modulation of the regioselectivity of a Bacillus α-galactosidase by direct evolution. Glycoconjugate J. 18 (2001) 215-223 and references therein
289. Spangenberg P., Andre C., Dion M., Rabiller C., and Mattes R. Comparative study of new α-galactosidases in transglycosylation reactions. Carbohydr. Res. 329 (2000) 65-73
290. Kim Y.W., Fox D.T., Hekmat O., Kantner T., McIntosh L.P., Warren R.A.J., and Withers S.G. Glycosynthase-based synthesis of xylo-oligosaccharides using an engineered retaining xylanase from Cellulomonas fimi. Org. Biomol. Chem. 4 (2006) 2025-2032