Variations on the SnCl4 and CF3CO2Ag-promoted glycosidation of sugar acetates: a direct, versatile and apparently simple method with either α or β stereocontrol

Carbohydrate Research

Volumn 344, Issue 13, 2009, Pages 1646-1653

  Xue, Jia Lu ^a,b   Cecioni, Samy ^a,b   He, Li ^a,b   Vidal, Sébastien ^a,b   Praly, Jean Pierre ^a,b  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

1,2 cis Glycosides; 1,2 trans Glycosides; Anomerization; Glycosylation; Peracetyl aldopyranoses; Silver trifluoroacetate; Tin tetrachloride

Indexed keywords

ACETYLATION; CHLORINE COMPOUNDS; GLYCOSYLATION; SILVER COMPOUNDS; TIN COMPOUNDS;

1,2-CIS-GLYCOSIDES; 1,2-TRANS-GLYCOSIDES; ANOMERIZATION; PERACETYL-ALDOPYRANOSES; SILVER TRIFLUOROACETATE;

FLUORINE COMPOUNDS;

ACETIC ACID; ALCOHOL; GLYCOSIDE; SUGAR; TIN CHLORIDE; ACETIC ACID DERIVATIVE; STANNIC CHLORIDE; TIN DERIVATIVE; TRIFLUOROACETIC ACID;

ACETYLATION; ANOMERIZATION; ARTICLE; CHEMICAL REACTION; DEACETYLATION; ELECTRON; FRAGMENTATION REACTION; GLYCOSIDATION; PRIORITY JOURNAL; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; GLYCOSYLATION; STEREOISOMERISM;

TETRA;

ACETATES; CATALYSIS; GLYCOSIDES; GLYCOSYLATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TIN COMPOUNDS; TRIFLUOROACETIC ACID;

EID: 69149101009     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.06.004     Document Type: Article

References (76)

1. In: Beat E., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology Vols. 1-4 (2000), Wiley-VCH, Weinheim
2. In: Fraser-Reid B.O., Tatsuta K., and Thiem J. (Eds). Glycoscience: Chemistry and Chemical Biology. 1st ed. Vols. 1-3 (2001), Springer, Berlin
3. In: Fraser-Reid B.O., Tatsuta K., Thiem J., Coté G.L., Flitsch S., Ito Y., Kondo H., Nishimura S., and Yu B. (Eds). Glycoscience: Chemistry and Chemical Biology. 2nd ed. Vols. 1-3 (2008), Springer, Berlin
4. In: Kamerling J.P., Boons G.J., Lee Y.C., Suzuki A., Taniguchi N., and Voragen A.G.J. (Eds). Comprehensive Glycoscience: from Chemistry to Systems Biology (2007), Elsevier, Oxford
5. Praly J.-P., He L., Qin B.B., Tanoh M., and Chen G.-R. Tetrahedron Lett. 46 (2005) 7081-7085
6. He L., Zhang Y.Z., Tanoh M., Chen G.-R., Praly J.-P., Chrysina E.D., Tiraidis C., Kosmopoulou M., Leonidas D.D., and Oikonomakos N.G. Eur. J. Org. Chem. (2007) 596-606
7. Zhang Y.Z., Aouadi K., Chen G.-R., and Praly J.-P. Synthesis (2007) 3473-3488
8. He L., Galland S., Dufour C., Chen G.-R., Dangles O., Fenet B., and Praly J.-P. Eur. J. Org. Chem. (2008) 1869-1883
9. Chen G.-R., and Praly J.-P. C. R. Chimie 11 (2008) 19-28
10. Kuribayashi T., Ohkawa N., and Satoh S. Tetrahedron Lett. 39 (1998) 4537-4540
11. Garegg P.J. Adv. Carbohydr. Chem. Biochem. 59 (2004) 69-134
12. Fügedi P. In: Levy D.E., and Péter Fügedi P. (Eds). The Organic Chemistry of Sugars (2006), CRC Taylor & Francis Group, Boca Raton 89-179
13. Fügedi P. In: Levy D.E., and Péter Fügedi P. (Eds). The Organic Chemistry of Sugars (2006), CRC Taylor & Francis Group, Boca Raton 181-221
14. Yu H., and Ensley H.E. Tetrahedron Lett. 44 (2003) 9363-9366
15. Kim J.-H., Yang H., and Boons G.-J. J. Am. Chem. Soc. 127 (2005) 12090-12097
16. Li N.-S., Lu J., and Piccirilli J.A. Org. Lett. 9 (2007) 3009-3012
17. Dong H., Pei Z., Byström S., and Ramström O. J. Org. Chem. 72 (2007) 1499-1502
18. Dong H., Pei Z., Angelin M., Byström S., and Ramström O. J. Org. Chem. 72 (2007) 3694-3701
19. Li Y., Tang P., Chen Y., and Yu B. J. Org. Chem. 73 (2008) 4323-4325
20. Crich D., and Karatholuvhu M.S. J. Org. Chem. 73 (2008) 5173-5176
21. Martin O.R. Carbohydr. Res. 171 (1987) 211-222
22. Adinolfi M., Iadonisi A., and Schiattarella M. Tetrahedron Lett. 44 (2003) 6479-6482
23. Okada Y., Nagata O., Taira M., and Yamada H. Org. Lett. 9 (2007) 2755-2758
24. Collot M., Savreux J., and Mallet J.-M. Tetrahedron 64 (2008) 1523-1535
25. Fairbanks A.J. Synlett (2003) 1945-1958
26. Cumpstey I. Carbohydr. Res. 343 (2008) 1553-1573
27. Demchenko A.V. Synlett (2003) 1225-1240
28. Demchenko A.V. Curr. Org. Chem. 7 (2003) 35-79
29. Robina I., Carmona A.T., and Moreno-Vargas A.J. Curr. Org. Synth. 5 (2008) 33-60
30. Lemieux R.U., and Shyluk W.P. Can. J. Chem. 31 (1953) 528-535
31. Hanessian S., and Banoub J. Carbohydr. Res. 59 (1977) 261-267
32. Banoub J., and Bundle D. Can. J. Chem. 57 (1979) 2085-2089
33. Mukaiyama T., Takashima T., Katsurada M., and Aizawa H. Chem. Lett. (1991) 533-536
34. Mukaiyama T., Katsurada M., and Takashima T. Chem. Lett. (1991) 985-988
35. Mukaiyama T., Shimpuku T., Takashima T., and Kobayashi S. Chem. Lett. (1989) 145-148
36. In: Crich D. (Ed). Handbook of Reagents for Organic Synthesis: Reagents for Glycoside, Nucleotide and Peptide Synthesis (2005), Wiley, Chichester 598-612 (a); pp. 613-614 (b)
37. O′Brien C., Poláková M., Pitt N., Tosin M., and Murphy P.V. Chem. Eur. J. 13 (2007) 902-909
38. Wang Y., Cheon H.-S., and Kishi Y. Chem. Asian J. 3 (2008) 319-326
39. Liu M.-Z., Fan H.-N., Guo Z.-W., and Hui Y.-Z. Chin. J. Chem. 14 (1996) 190-192
40. Liu M.-Z., Fan H.-N., Guo Z.-W., and Hui Y.-Z. Carbohydr. Res. 290 (1996) 233-237
41. Aich U., and Loganathan D. Carbohydr. Res. 341 (2006) 19-28
42. Aich U., and Loganathan D. Carbohydr. Res. 342 (2007) 704-709
43. Collins P.M., Overend W.G., and Rayner B.A. Carbohydr. Res. 31 (1973) 1-16
44. Hanessian S., and Kagotani M. Carbohydr. Res. 202 (1990) 67-69
45. Hickinbottom W.J. J. Chem. Soc. (1928) 3140-3147
46. Hickinbottom W.J. J. Chem. Soc. (1930) 1338-1348
47. Haines A.H. Adv. Carbohydr. Chem. Biochem. 3 (1981) 13-70
48. Li J., and Wang Y. Synth. Commun. 34 (2004) 211-217
49. van Well R.M., Kartha K.P.R., and Field R.A. J. Carbohydr. Chem. 24 (2005) 463-474
50. Konstantinovic S., Predojevic J., Mojsilovic B., Dimitrijevic B., and Milosevic G. Ind. J. Chem. 40B (2001) 796-801
51. Wolfrom M.L., Thompson A., and Lineback D.R. J. Org. Chem. 28 (1963) 860-861
52. α-anomer:. Ferrier R.J., Hay R.W., and Vethaviyasar N. Carbohydr. Res. 27 (1973) 55-61
53. β-anomer:. Mukherjee D., Ray P.K., and Chowdhury U.S. Tetrahedron 57 (2001) 7701-7704
54. α-anomer:. Roy B., and Mukhopadhyay B. Tetrahedron Lett. 48 (2007) 3783-3787
55. β-anomer:. Kishida M., and Akita H. Tetrahedron 61 (2005) 10559-10568
56. α-, and β-anomers:. Yuasa Y., and Yuasa Y. Org. Process Res. Dev. 8 (2004) 405-407
57. Pastore A., Adinolfi M., and Iadonisi A. Eur. J. Org. Chem. (2008) 6206-6212
58. Ramza J., Descotes G., Basset J.-M., and Mutch A. J. Carbohydr. Chem. 15 (1996) 125-136
59. Bock K., Lundt I., and Pedersen C. Tetrahedron Lett. 13 (1973) 1037-1040
60. Bock K., and Pedersen C. Adv. Carbohydr. Chem. Biochem. 41 (1983) 27-66 and references cited therein
61. Nóbrega C., and Vázquez J.T. Tetrahedron: Asymmetry 14 (2003) 2793-2801
62. Nowacki A., Smiataczowa K., Kasprzykowska R., Dmochowska B., and Wisniewski A. Carbohydr. Res. 337 (2002) 265-272
63. Veyrières A. In: Beat E., Hart G.W., and Sinaÿ P. (Eds). Carbohydrates in Chemistry and Biology. Chemistry of Saccharides Vol. 1 (2000), Wiley-VCH, Weinheim 367-405
64. Marzabadi C.H., and Franck R.W. Tetrahedron 56 (2000) 8385-8417
65. Preparation of glycosylated bioactive peptide drugs with prolonged duration of action. Sandoz AG, PCT Int. Appl. 1988, 147 pp. CODEN: PIXXD2 WO 8802756 A2 19880421 Chem. Abstr. Nber 110:213349 AN 1989:213349.
66. Chernyak A.Y., Sharma G.V.M., Kononov L.O., Krishna P.R., Levinsky A.B., and Kochetkov N.K. Carbohydr. Res. 223 (1992) 303-309
67. Mereyala H.B., and Gurrala S.R. Carbohydr. Res. 307 (1998) 351-354
68. Wang J., Zhang B., Fang J., Sujino K., Li H., Otter A., Hindsgaul O., Palcic M.M., and Wang P.G. J. Carbohydr. Chem. 22 (2003) 347-376
69. Koshi Y., Nakata E., Miyagawa M., Tsukiji S., Ogawa T., and Hamachi I. J. Am. Chem. Soc. 130 (2008) 245-251
70. Rajca A., and Wiessler M. Carbohydr. Res. 274 (1995) 123-136
71. Listkowski A., Ing P., Cheaib R., Chambert S., Doutheau A., and Queneau Y. Tetrahedron: Asymmetry 18 (2007) 2201-2210
72. Pierre R., Chambert S., Alirachedi F., Danel M., Trombotto S., Doutheau A., and Queneau Y. C.R. Chimie 11 (2008) 61-66
73. Yamasaki, M.; Suzawa, T.; Murakami, T.; Sakurai, N. Ointments Containing Polyalkylene Glycol Derivative-modified Biologically Active Polypeptides. PCT Int. Appl. (2003), 165 pp. CODEN: PIXXD2 WO 2003000278 A1 20030103 CAN 138:78455 AN 2003:5795.
74. Murakami T., Hirono R., Sato Y., and Furusawa K. Carbohydr. Res. 342 (2007) 1009-1020
75. Vatèle J.-M., Fenet B., and Eynard T. Chem. Phys. Lipids 94 (1998) 239-250
76. Bols M., and Hansen H.C. Acta Chem. Scand. 47 (1993) 818-822