Regio- and stereoselective synthesis of oligosaccharides with acetobromolactose and acetobromomaltose as glycosyl donors via orthoester intermediates

Journal of Carbohydrate Chemistry

Volumn 18, Issue 4, 1999, Pages 451-460

  Wang, Wei ^a   Kong, Fanzuo ^a  

^a RESEARCH CENTER FOR ECO ENVIRONMENTAL SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033241393     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309908544009     Document Type: Article

References (16)

1. W. Wang and F. Kong, J. Org. Chem., 63, 5744 (1998).
2. About preparation of orthoesters with disaccharide donors: (a) P.H. Seeberger, M. Eckhardt, C.E. Gutteridge, and S.J. Danishefsky, J. Am. Chem. Soc., 119, 10064 (1997).
3. (b) J. Banoub and D.R. Bundle, Can. J. Chem., 57, 209 (1979).
4. (c) S.E. Zurabyan, M.M. Tikhomirov, V.A. Nesmeyanov, and A.Y. Khorlin, Carbohydr. Res., 26, 117 (1973).
5. (d) N.K. Kochetkov, A.J. Khorlin, and A.F. Bochkov, Tetrahedron, 23, 693 (1967).
6. (a) K. Suzuki and T. Matsumoto, Yuki Gosei Kagaku Kyokaishi, 51, 718 (1993).
7. (b) C. Unverzagt, Angew. Chem. Int. Ed. Engl., 33, 1102 (1994).
8. (c) R. Verduyn, M. Douwes, P.A.M. van der Klein, E.M. Moesinger, G.A. van der Marel, and J.H. van Boom, Tetrahedron, 49, 7301 (1993).
9. (d) X.-B. Han, Z.-H. Jiang, and R.R. Schmidt, Liebigs Ann. Chem., 853 (1993).
10. H. Paulsen and J.P. Lorentzen, Carbohydr. Res., 140, 155 (1985).
11. About rearrangement of sugar-sugar orthoesters (a) J. Gass, M. Strobl, A. Loibner, P. Kosma, and U. Zähringer, Carbohydr. Res., 244, 69 (1993).
12. (b) M.L. Sznaidman, S.C. Johnson, C. Crasto, and S.M. Hecht, J. Org. Chem., 60, 3942 (1995).
13. (c) T. Ogawa, K. Beppu, and S. Nakabayashi, Carbohydr. Res., 93, C6 (1981).
14. D.J. Jenkins and B.V.L. Potter, Carbohydr. Res., 287, 169 (1996).
15. (a) W. Wang and F. Kong, Tetrahedron Lett., 39, 1937 (1998).
16. (b) F. Kong and W. Wang, Chinese Patents, Appl. 971257788.4, 98103242.7, 98103241.9.