Thioglycosylation of 1,2-cis-glycosyl acetates: A long-standing overlooked issue in preparative carbohydrate chemistry

Carbohydrate Research

Volumn 346, Issue 9, 2011, Pages 1149-1153

  Xu, Ci ^a   Liu, Han ^a   Li, Xuechen ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

1,2 cis Glycosyl acetates; Lewis acid catalyzed thioglycosylation; Thioglycoside

Indexed keywords

1,2-CIS-GLYCOSYL ACETATES; CARBOHYDRATE CHEMISTRY; CATALYTIC AMOUNTS; DIRECT CONVERSION; GLYCOSYL ACETATE; IMPURITIES IN; LEWIS ACID; LEWIS ACIDS; REACTION TEMPERATURE; THIOGLYCOSIDES;

CARBOHYDRATES;

CATALYSIS;

1,2 CIS GLYCOSYL ACETATE DERIVATIVE; ACETIC ACID DERIVATIVE; ALPHA GLYCOSYL ACETATE DERIVATIVE; GLUCOPYRANOSIDE; LEWIS ACID; PHENYL 2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 2,3,4,6 TETRA O ACETYL 1 THIO BETA DEXTRO GALACTOPYRANOSIDE; PHENYL 2,3,4,6 TETRA O ACETYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 3,4,6 TRI O ACETYL 2 DEOXY 2 N TETRACHLOROPHTHALIMIDO 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CARBOHYDRATE ANALYSIS; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; GLYCOSYLATION; PRIORITY JOURNAL; TEMPERATURE MEASUREMENT; THIOGLYCOSYLATION;

ACETATES; CARBOHYDRATE CONFORMATION; GALACTOSIDES; GLUCOSIDES; GLYCOSYLATION; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 79955936548     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2011.03.033     Document Type: Article

References (32)

1. For reviews, see: (a) Codée, J. D. C.; Litjens, R. E. J. N.; van den Bos, L. J.; Overkleeft, H. S.; van der Marel, G. A. Chem. Soc. Rev. 2005, 34, 769-782;
2. (b) Garegg, P. J. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179-205.
3. For a review, see: Ferrier, R.; Furneaux, R. Methods Carbohydr. Chem. 1980, 8, 251-253.
4. For examples, see: (a) Fischer, E.; Delbrück, K. Ber. Dtsch. Chem. Ges. 1909, 42, 1476-1482;
5. (b) Apparu, M.; Blanc-Muesser, M.; Defaye, J.; Driguez, H. Can. J. Chem. 1981, 59, 314-320;
6. (c) Tropper, F. D.; Andersson, F. O.; Grand-Maître, C.; Roy, R. Synthesis 1991, 734-736;
7. (d) Horton, D. Methods Carbohydr. Chem. 1963, 2, 433-437.
8. Edward, J. T. Chem. Ind. (London) 1955, 1102-1104.
9. (a) Jensen, H. H.; Bols, M. Org. Lett. 2003, 5, 3419-3421;
10. (b) McDonnell, C.; López, O.; Murphy, P.; Bolaños, J. G. F.; Hazell, R.; Bols, M. J. Am. Chem. Soc. 2004, 126, 12374-12385;
11. (c) Pedersen, C. M.; Marinescu, L. G.; Bols, M. Chem. Commun. 2008, 2465-2467;
12. (d) Henekendorff, M.; Pedersen, C. M.; Bols, M. Chem. Eur. J. 2010, 16, 13982-13994.
13. 2-catalyzed thioglycosylation, see: (a) Ferrier, R. J.; Furneaux, R. H. Carbohydr. Res. 1976, 52, 63-68;
14. (b) Janczuk, A. J.; Zhang, W.; Andreana, P. R.; Warrick, J.; Wang, P. G. Carbohydr. Res. 2002, 337, 1247-1259;
15. (c) Fukunaga, K.; Yoshida, M.; Nakajima, F.; Uematsu, R.; Hara, M.; Inoue, S.; Kondo, H.; Nishimura, S.-I. Bioorg. Med. Chem. Lett. 2003, 13, 813-815;
16. (d) Cheng, M. S.; Wang, Q. L.; Tian, Q.; Song, H. Y.; Liu, Y. X.; Li, Q.; Xu, X.; Miao, H. D.; Yao, X. S.; Yang, Z. J. Org. Chem. 2003, 68, 3658-3662;
17. (e) Boulineau, F. P.; Wei, A. J. Org. Chem. 2004, 69, 3391-3399;
18. (f) Hasegawa, J.; Hamada, M.; Miyamoto, T.; Nishide, K.; Kajimoto, T.; Uenishi, J.; Node, M. Carbohydr. Res. 2005, 340, 2360-2368;
19. (g) Denmark, S. E.; Kobayashi, T.; Regens, C. S. Tetrahedron 2010, 66, 4745-4759.
20. For a review, see: Norberg, T. In Modern Methods in Carbohydrate Synthesis; Kahn, S. H., O'Neil, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996; pp 82-106. and references cited therein.
21. 3-catalyzed thioglycosylation, see: Dasgupta, F.; Garegg, P. J. Acta Chem. Scand. 1989, 43, 471-475.
22. Probably for this reason, many newly developed Lewis-acid-catalyzed thioglycosylations used 1,2-trans-glycosyl acetates (e.g., β-1-acetate glucose), see: (a) Das, S. K.; Roy, J.; Reddy, K. A.; Abbineni, C. Carbohydr. Res. 2003, 338, 2237-2240;
23. (b) Ibatullin, F. M.; Shabalin, K. A.; Janis, J. V.; Shavva, A. G. Tetrahedron Lett. 2003, 44, 7961-7964;
24. (c) Weng, S.-S.; Lin, Y.-D.; Chen, C.-T. Org. Lett. 2006, 8, 5633-5636;
25. (d) Weng, S.-S. Tetrahedron Lett. 2009, 50, 6414-6417.
26. Seibel, J.; Hillringhaus, L.; Moraru, R. Carbohydr. Res. 2005, 340, 507-511.
27. Wolfrom, M. L.; Thompson, A. Methods Carbohydr. Chem. 1963, 2, 211-215.
28. For comments on the acidity of Lewis acids, see: (a) Laszlo, P.; Teston, M. J. Am. Chem. Soc. 1990, 112, 8750-8754;
29. (b) Kobayashi, S.; Busujima, T.; Nagayama, S. Chem. Eur. J. 2000, 6, 3491-3494.
30. Kappe, O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, 2005.
31. Olsson, L.; Kelberlau, S.; Jia, Z. J.; Fraser-Reid, B. Carbohydr. Res. 1998, 314, 273-276.
32. Benakli, K.; Zha, C.; Kerns, R. J. J. Am. Chem. Soc. 2001, 123, 9461-9462.