AN EXTREMELY MILD AND STEREOCONTROLLED CONSTRUCTION OF 1,2-TRANS-BETA-GLYCOSIDIC LINKAGES CAPITALIZING ON BENZYL-PROTECTED GLYCOPYRANOSYL DIETHYL PHOSPHITES AS GLYCOSYL DONORS

Authors
HASHIMOTO S UMEO K SANO A WATANABE N NAKAJIMA M IKEGAMI S
Citation
S. Hashimoto et al., AN EXTREMELY MILD AND STEREOCONTROLLED CONSTRUCTION OF 1,2-TRANS-BETA-GLYCOSIDIC LINKAGES CAPITALIZING ON BENZYL-PROTECTED GLYCOPYRANOSYL DIETHYL PHOSPHITES AS GLYCOSYL DONORS, Tetrahedron letters, 36(13), 1995, pp. 2251-2254
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
13
Year of publication
1995
Pages
2251 - 2254
Database
ISI
SICI code
0040-4039(1995)36:13<2251:AEMASC>2.0.ZU;2-J
Abstract
A highly stereocontrolled 1,2-trans-beta-glycosidation reaction withou t neighboring group participation has been developed by using benzyl-p rotected glycopyranosyl diethyl phosphites as glycosyl donors and boro n trifluoride etherate as a promoter. The present method exhibits the highest level of 1,2-trans-beta-selectivity known to date for glycosid ations with a non-participating group on O-2.