Catalytic glycosylation with glycosyl thioimidate donors

European Journal of Organic Chemistry

Volumn , Issue 26, 2008, Pages 4401-4404

  Lucas Lopez, Cristina ^a   Murphy, Niamh ^a   Zhu, Xiangming ^a,b  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

Carbohydrates; Catalytic activation; Glycosylation; Sulfur

Indexed keywords

EID: 53849115759     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800503     Document Type: Article

References (28)

1. A. Michael, Am. Chem. J. 1879, 1, 305-312.
2. F. Fischer, Ber. Dtsch. Chem. Ges. 1893, 26, 2400-2412.
3. W. Koenigs, E. Knorr, Ber. Dtsch. Chem. Ges. 1901, 34, 957-981.
4. A. V. Demchenko (Ed.), Handbook of Chemical Glycosylation, Wiley-VCH, Weinheim, 2008.
5. X. Zhu, R. R. Schmidt, Angew. Chem. Int. Ed., manuscript submitted.
6. R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl. 1980, 19, 731-733.
7. R. R. Schmidt, W. Kinzy, Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
8. a) R. R. Schmidt, J. Michel, M. Roos, Liebigs Ann. Chem. 1984, 1343-1357;
9. b) U. Huchel, Dissertation, University of Konstanz, 1998, Papierflieger, Clausthal-Zellerfeld (ISBN 3-89720-221-2).
10. For some recent examples, see: a) S. I. Tanaka, M. Takashina, H. Tokimoto, Y. Fujimoto, K. Tanaka, K. Fukase, Synlett 2005, 2325-2328;
11. b) H. Tanaka, Y. Iwata, D. Takahashi, M. Adachi, T. Takahashi, J. Am. Chem. Soc. 2005, 127, 1630-1631;
12. c) D. Comegna, E. Bedini, A. D. Nola, A. Iadonisi, M. Parrilli, Carbohydr. Res. 2007, 342, 1021-1029;
13. d) M. Thomas, J. P. Gesson, S. Papot, J. Org. Chem. 2007, 72, 4262-4264.
14. a) G. J. S. Lohman, P. H. Seeberger, J. Org. Chem. 2004, 69, 4081-4093;
15. b) P. Bindschädler, C. Noti, E. Castagnetti, P. H. Seeberger, Helv. Chim. Acta 2006, 89, 2591-2610.
16. a) H. Zinner, K. Peseke, Chem. Ber. 1965, 98, 3508-3514;
17. b) P. Nuhn, G. Wagner, Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1968, 301, 186-200.
18. R. B. Woodward, E. Logusch, K. P. Nambiar, K. Sakan, D. E. Ward, B. W. Au-Yeung, P. Balaram, L. J. Browne, P. J. Card, C. H. Chen, R. B. Chenevert, A. Fliri, K. Frobel, H. J. Gais, D. G. Garratt, K. Hayakawa, W. Heggie, D. P. Hesson, D. Hoppe, I. Hoppe, J. A. Hyatt, D. Ikeda, P. A. Jacobi, K. S. Kim, Y. Kobuke, K. Kojima, K. Krowicki, V. J. Lee, T. Leutert, S. Malchenko, J. Martens, R. S. Matthews, B. S. Ong, J. B. Press, T. V. Rajan Babu, G. Rousseau, H. M. Sauter, M. Suzuki, K. Tatsuta, L. M. Tolbert, E. A. Truesdale, I. Uchida, Y. Ueda, T. Uyehara, A. T. Vasella, W. C. Vladuchick, P. A.Wade, R. M. Williams, H. N. C. Wong, J. Am. Chem. Soc. 1981, 103, 3215-3217.
19. A. Ramakrishnan, P. Pornsuriyasak, A. V. Demchenko, J. Carbohydr. Chem. 2005, 24, 649-663.
20. a) A. V. Demchenko, M. N. Kamat, C. De Meo, Synlett 2003, 1287-1290;
21. b) A. V. Demchenko, N. N. Malysheva, C. De Meo, Org. Lett. 2003, 5, 455-458.
22. A. V. Demchenko, P. Pornsuriyasak, C. De Meo, N. N. Malysheva, Angew. Chem. Int. Ed. 2004, 43, 3069-3072.
23. a) P. Pornsuriyasak, U. B. Gangadharmath, N. P. Rath, A. V. Demchenko, Org. Lett. 2004, 6, 4515-4518;
24. b) P. Pornsuriyasak, A. V. Demchenko, Chem. Eur. J. 2006, 12, 6630-6646.
25. B. Yu, H. Tao, J. Org. Chem. 2002, 67, 9099-9102.
26. The preparation of glycosyl thiol dates from nearly half a century ago and new preparative procedures are still emerging: a) M. Černý, J. Vrkoč, J. Staněk, J. Collect. Czech. Chem. Commun. 1959, 24, 64-69;
27. b) G. J. L. Bernardes, D. P. Gamblin, B. G. Davis, Angew. Chem. Int. Ed. 2006, 45, 4007-4011.
28. It is worth mentioning that very recently we developed a stereospecific procedure for the synthesis of á-glycosyl thiols, see: R. T. Dere, Y. Wang, X. Zhu, Org. Biomol. Chem. 2008, 6, 2061-2063.