Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis

Chemistry - A European Journal

Volumn 15, Issue 41, 2009, Pages 10972-10982

  Chao, Chin Sheng ^a   Li, Chen Wei ^a   Chen, Min Chun ^a   Chang, Shih Sheng ^a   Mong, Kwok Kong Tony ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

Carbohydrates; Glycosylation; Neighboring group effects; Stereoselectivity; Substrate concentration

Indexed keywords

CARBOHYDRATE CHEMISTRY; GLYCOSIDIC BOND; GLYCOSYL; GLYCOSYLATION REACTIONS; LOW CONCENTRATIONS; NEIGHBORING-GROUP EFFECTS; NEW STRATEGY; OLIGOSACCHARIDE SYNTHESIS; SUBSTRATE CONCENTRATION; SUBSTRATE CONCENTRATIONS; THIOGLYCOSIDES;

CARBOHYDRATES; CONCENTRATION (PROCESS); ESTERIFICATION; GLYCOSYLATION; OLIGOSACCHARIDES; STEREOSELECTIVITY;

SUBSTRATES;

EID: 70350233347     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901119     Document Type: Article

References (86)

1. a) A. V. Demchenko, Curr. Org. Chem. 2003, 7, 35-79;
2. b) J. D.C. Codée, E. J. N. Litjens, L. J. van den Bos, H. S. Overkleeft, G. A. van der Marel, Chem. Soc. Rev. 2005, 34, 769-782;
3. Y. Wang, X.-S. Ye, L.-H. Zhang, Org. Biomol. Chem. 2007, 5, 2189-2200.
4. a) L. Goodman, Adv. Carbohydr. Chem. Biochem. 1967, 22, 109-175;
5. b) G. Wulff, G. Rühle, Angew. Chem. 1974, 86, 173-187;
6. Angew. Chem. Int. Ed. Engl. 1974, 13, 157-170;
7. B. Capon, S. P. McManus, Neighboring Group Participation, Plenum Press, New York, 1976;
8. D. Crich, T.-S. Hu, F. Cai, J. Org. Chem. 2008, 73, 8942-8953.
9. a) B. Fraser-Reid, S. Grimme, M. Piacenza, M. Mach, U. Schlueter, Chem. Eur. J. 2003, 9, 4687-4692;
10. b) M. Dubber, O. Sperling, T. K. Lindhorst, Org. Biomol. Chem. 2006, 4, 3901-3912;
11. F. Kong, Carbohydr. Res 2007, 342, 345-373.
12. a) T. Nukada, A. Berces, M. Z. Zgierski, D. M. Whitfield, J. Org. Chem. 1999, 64, 9030-9045;
13. b) Z. Li, J. C. Gildersleeve, J. Am. Chem. Soc. 2006, 128, 11612-11619;
14. M. U. Roslund, O. Aitio, J. Wärnå, H. Maaheimo, D-Y. Murzin, R. Leino, J. Am. Chem. Soc. 2008, 130, 8769-8772.
15. F. Belot, J.-C. Jacquinet, Carbohydr. Res 1996, 290, 79-86.
16. A. P. Doerschuk, J. Am,. Chem,. Soc. 1952, 74, 4202-4203.
17. a) H. Kunz, W Sager, Helv. Chim. Acta, 1985, 68, 283-287;
18. b) L. Yan, D. Kahne, J. Am. Chem. Soc. 1996, 118, 9239-9248.
19. a) H.-L. Jiao, O. Hindsgaul, Angew. Chem. 1999, 111. 421-424;
20. Angew. Chem. Int. Ed. 1999, 38, 346-348;
21. b) J. T. Smoot, P. Pornsuriyasak, A. V. Demchenko, Angew. Chem. 2005, 117, 7285-7288;
22. Angew. Chem,. Int. Ed. 2005, 44, 7123-7126;
23. J.-H. Kim, H. Yang, G.-J. Boons, Angew. Chem. 2005, 117, 969-971;
24. Angew. Chem. Int. Ed, 2005, 44, 947-949;
25. T. Yamada, K. Takemura, J.-I. Yoshida, S. Yamago, Angew. Chem,. 2006, 118, 7737-7740;
26. Angew. Chem. Int. Ed, 2006, 45, 7575-7578.
27. a) S.-I. Hashimoto, K. Umeo, A. Sano, N. Watanabe, M, Nakajima, S. Ikegami, Tetrahedron Lett 1995, 36, 2251-2254, and references therein;
28. b) T. Mukaiyama, T. Hashihayata, H. Mandai, Chem. Lett. 2003, 32, 340-341;
29. H. Tanaka, A. Yoshizawa, T. Takahashi, Angew. Chem. 2007, 119, 2557-2559;
30. Angew. Chem,. Int. Ed. 2007, 46, 2505-2507.
31. a) D. Crich, P. Jayalath, J. Org. Chem. 2005, 70, 7252-7259;
32. b) D. Crich, V. Subramanian, T. K. Hutton, Tetrahedron 2007, 63, 5042-5049.
33. S.-S. Kulkami, Y-H. Liu, S.-C. Hung, J. Org. Chem. 2005, 70, 2808-2811.
34. a) Y. Ito, T. Ogawa, Tetrahedron Lett. 1987, 28, 4701-4704;
35. b) I. Braccini, C. Derouet, J. Esnault, C. Hervé du Penhoat, J.-M. Mallet, V. Michon, P. Sinaÿ, Carbohydr. Res. 1993, 246, 23-41;
36. R. R. Schmidt, M. Behrendt, A. Toepfer, Synlett 1990, 694-696;
37. Y. D. Vankar, P. S. Vamkar, M. Behrendt, R. R. Schmidt, Tetrahedron 1991, 47, 9985-9992;
38. e) T. Tsuda, S. Nakamura, S. Hashimoto, Tetrahedron 2004, 60, 10711-10737;
39. f) S. Hashimoto, M, Hayashi, R. Noyori, Tetrahedron Lett. 1984, 25, 1379-1382;
40. g) A. J. Ratcliffe, B. Fraser-Reid, J. Chem Soc. Perkin Trans. 1 1990, 747-750.
41. E. A. Mensah, J. M. Azzarelli, H. M. Nguyen, J. Org. Chem. 2009, 74, 1650-1657.
42. a) H. Tanaka, T. Amaya, T. Takahashi, Tetrahedron Lett. 2003, 44, 3053-3057;
43. b) S. Shahinian, H. Bussey, Mol. Microbiol. 2000, 35, 477-489.
44. a) H. Farkas-Himsley, R. Hill, B. Rosen, S. Arab, C. A. Lingwood, Proc. Natl. Acad Sci. USA 1995, 92, 6996;
45. b) E. Fan, E. A. Merritt, C. L. M. J. Verlinde, W. G. J. Hol, Curr. Opin. Struct. Biol. 2000, 10, 680-686;
46. P. I. Kitov, H. Shimizu, S. W Homans, D. R. Bundles, J. Am. Chem. Soc. 2003, 125, 3285-3294, and references therein.
47. a) K. A. Karlsson, Pure Appl. Chem. 1987, 59, 1447-1448;
48. b) I. G. Dale, G. P. Daniel, M. J. Smith, Science 2004, 306, 1687-1689.
49. Preparations of thioglycosyl donors, glycon and aglycon acceptors in this study were detailed in the Supporting Information.
50. a) G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 31, 1331-1334;
51. b) H. Ito, H. Ishida, M. Kiso, A. Hasegawa, Carbohydr. Res. 1991, 304, 187-189.
52. a) O. J. Plante, E. R. Palmacci, P. H. Seeberger, Science 2001, 291, 1523;
53. b) L. Rontenberg Love, P. H. Seeberger, Angew. Chem. 2004, 116, 612-615;
54. Angew. Chem. Int. Ed. 2004, 43, 602-605.
55. a) Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Bassov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753;
56. b) K.-K. T. Mong, C.Y. Huang, C.-H. Wong, J. Org. Chem. 2003, 68, 2135-2142.
57. D. M. Ratner, E. R. Murthy, M. Jhunjhunwala, D. A. Synder, K. F. Jensen, P. H. Seeberger, Chem. Commun. 2005, 578-580.
58. a) L. Drouin, R. G. Compton, N. Fietkau, A. J. Fairbanks, Synlett 2007, 2711-2717, and references therein;
59. b) T. Nokami, A. Shibuya, H. Tsuyama, S. Suga, A. A. Bowers, D. Crich, J. Yoshida, J. Am Chem. Soc. 2007, 129, 10922-10928.
60. R.-M. van Well, T. S. Kärkkäinen, K.P. Ravindranathan Kartha, R. A. Field, Carbohydr. Res. 2006, 341, 1391-1397.
61. A. Ueki, M. Hirota, Y. Kobayashi, K. Komatsu, Y. Takano, M. Iwaoka, Y. Nakahara, H. Hojo, Y. Nakahara, Tetrahedron 2008, 64, 2611-2618.
62. A. Demchenko, T. Stauch, G.-I. Boons, Synlett 1997, 818-820.
63. D. R. Mootoo, P. Konradsson, U. E. Udodong, B. Fraser-Reid, J. Am. Chem. Soc. 1988, 110, 5583-5584.
64. R. E. Pincock, T. E. Kivosky, J. Chem. Educ. 1966, 43, 358-360.
65. 3CN-EtCN mixture is lower than -78°C and no further observation was made below that temperature.
66. a) R. R. Schmidt, A. Toepfer, Tetrahedron Lett. 1991, 32, 3353;
67. b) J. G. Taylor, X.-C. Li, M. Oberthür, W-J. Zhu, D. E. Kahne, J. Am. Chem. Soc. 2006, 128, 15084-15085, and reference therein.
68. a) J. M. Lassaletta, K, Carlsson, P. J. Garegg, R. R. Schmidt, J. Org. Chem. 1996, 61, 6873-6880;
69. b) X.-S. Ye, C-H. Wong, J. Org. Chem. 2000, 65, 2410;
70. L. Chen, F. Kong, Tetrahedron Lett. 2003, 44, 3691-3695;
71. C.-Y. Huang, D-A. Thayer, A.-Y. Chang, M.-D. Best, J. Hoffmann, S. Head, C.-H. Wong, Proc. Natl. Acad. Sci. USA 2006, 103, 15-20.
72. Preparation of allyl serine ester 31: B. de La Torre, J. L. Torres, E. Bardaji, P. Clapés, N. Xaus, X. Jorba, S. Calvet, F. Albericio, G. Valencia, J. Chem. Soc. Chem. Commun. 1990, 965-967.
73. A. Rencurosi, L. Lay, G. Russo, E. Caneva, L. Poletti, J. Org. Chem. 2005, 70, 7765-7768.
74. G. O. Aspinall, M. A. Monteiro, H. Pang, E. J. Walsh, A. P. Moran, Biochemistry 1996, 35, 2489-2497.
75. "Solutions and Non-Covalent Binding Forces": E. V. Anslyn, D. A. Dougherty in Modern Physical Organic Chemistry, University Science Books, California, 2006, pp. 145-206.
76. D. Crich, S. Sun, J. Am. Chem. Soc. 1997, 119, 11217-11223.
77. a) "Stereoelectronic Effects in Organic Chemistry": P. Deslongchamps in Organic Chemistry Series, Vol.1, Pergamon Press, Oxford, 1983;
78. b) A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, Berlin, 1983.
79. a) C. L. Perrin, Tetrahedron 1995, 51, 11901-11935;
80. b) C. L. Perrin, M. A. Fabian, J. Brunckova, B. K. Ohta, J. Am. Chem. Soc. 1999, 121, 6911-6918;
81. C. L. Perrin, J. Kuperman, J. Am. Chem. Soc. 2003, 125, 8846-8851.
82. Failure to acquire NMR spectra for a-glycosyl nitrilium at low temperatures was also reported: D. Crich, M. Patel, Carbohydr. Res. 2006, 341, 1461-1475.
83. a) S.-Y. Hsieh, M.-D. Jan, L.-N. Patkar, C.-T. Chen, C.-C. Lin, Carbohydr. Res. 2005, 340, 49-57;
84. b) M.R.E. Aly, P. Rochaix, M. Amessou, L. Johannes, J.-C. Florent, Carbohydr. Res. 2006, 341, 2026-2036;
85. C.-N. Wang, Q. Li, H.-S. Wang, L.-H. Zhang, X.-S. Ye, Tetrahedron 2006, 62, 11657-11662, and references therein.
86. X. Zhu, S. Kawatkar, Y. Rao, G.-J. Boons, J. Am. Chem. Soc. 2006, 128, 11948-11957.