Vinyl glycosides in oligosaccharide synthesis (part 6): 3-Buten-2-YL 2-azido-2-deoxy glycosides and 3-buten-2-YL 2-phthalimido-2-deoxy glycosides as novel glycosyl donors

Journal of Carbohydrate Chemistry

Volumn 19, Issue 7, 2000, Pages 939-958

  Bai, Yu ^a   Boons, Geert Jan ^a,b   Burton, Andrew ^a   Johnson, Matthew ^a   Haller, Michael ^a,b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034369708     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328300008544127     Document Type: Article

References (29)

1. a) G.-J. Boons and S. Isles, Tetrahedron Lett., 35, 3593 (1994);
2. b) G.-J. Boons and S. Isles, J. Org. Chem., 61, 4262 (1996);
3. c) G.-J. Boons, R. Gibson and R. Dickinson, J. Chem. Soc., Perkin Trans. 1, 3357 (1997).
4. a) G.-J. Boons, B. Heskamp and F. Hout, Angew. Chem. Int. Ed. Engl., 35, 2845 (1996);
5. b) M. Johnson, C. Aries and G.-J. Boons, Tetrahedron Lett., 39, 9801 (1998).
6. J. Banoub, P. Boullanger and D. Lafont, Chem. Rev., 92, 1167 (1992).
7. J. Debenham, R. Rodebaugh and B. Fraser-Reid, Liebigs Ann./Recueil, 791 (1997).
8. D. R. Bundle and S. Josephson, Can. J. Chem., 57, 662 (1979).
9. P. L. Durette, E. P. Meitzner and T. Y. Shen, Tetrahedron Lett., 42, 4013 (197.
10. R. Madsen, U. E. Udodong, C. Roberts, D. R. Mootoo, P. Konradsson and B Fraser-Reid, J. Am. Chem. Soc., 117, 1554 (1995).
11. J. O. Osby, M. G. Martin and B. Ganem, Tetrahedron Lett., 25, 2093 (1984).
12. P. Stangier and O. Hindsgaul, Synlett, 179 (1996).
13. H. Paulsen, Angew. Chem. Int. Ed. Engl., 21, 155 (1982).
14. A. Vasella, C. Witzig, J.-L. Chiara and M. Martin-Lomas, Helv. Chim. Acta, 74, 2073 (1991).
15. P. B. Alper, S.-C. Hung and C.-H. Wong, Tetrahedron Lett., 34, 6029 (1996).
16. B. Yu, Q. Oujang, C. Li and Y. Hui, J. Carbohydr. Chem., 15, 297 (1996).
17. S. Fujita, M. Numata, M. Sugimoto, K. Tomita and T. Ogawa, Carbohydr. Res 228, 347 (1992).
18. G.-J. Boons, A. Burton and S. Isles, Chem. Commun., 141 (1996).
19. C. Lamberth and M.D. Bednarski, Tetrahedron Lett., 50, 7369 (1991).
20. a) R. R. Schmidt and J. Michel, J. Carbohydr. Chem., 4, 141 (1985);
21. b) R. R. Schmidt, M. Behrendt and A. Toepfer, Synlett, 694 (1990);
22. c) Y. D. Vankar, P. S. Vankar, M. Behrendt and R. R. Schmidt, Tetrahedron, 47, 9985 (1991);
23. d) R. R. Schmidt, H. Gaden and H. Jatzke, Tetrahedron Lett., 31, 327 (1990);
24. Others have also employed glycopyranosyl acetonitrilium-ions in carbohydrate chemistry. For example see: a) J. Pougny and P, Sinaÿ, Tetrahedron Lett., 4073 (1976);
25. b) R. U. Lemieux and R. M. Ratcliffe, Can. J. Chem., 57, 1244 (1979);
26. c) A. I. Ratcliffe and B. Fraser-Reid, J. Chem. Soc., Perkin. Trans. 1, 747 (1990).
27. A. Demchenko and G.-J. Boons, Synlett, 818 (1997).
28. R. U. Lemieux, Can. J. Chem., 60, 58 (1982).
29. P. J. Garegg, H. Hultberg and S. Wallin, Carbohydr. Res., 108, 97 (1982).