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

被引:66
作者
HASHIMOTO, S [1 ]
UMEO, K [1 ]
SANO, A [1 ]
WATANABE, N [1 ]
NAKAJIMA, M [1 ]
IKEGAMI, S [1 ]
机构
[1] TEIKYO UNIV,FAC PHARMACEUT SCI,SAGAMIKO,KANAGAWA 19901,JAPAN
关键词
D O I
10.1016/0040-4039(95)00263-C
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly stereocontrolled 1,2-trans-beta-glycosidation reaction without neighboring group participation has been developed by using benzyl-protected glycopyranosyl diethyl phosphites as glycosyl donors and boron trifluoride etherate as a promoter. The present method exhibits the highest level of 1,2-trans-beta-selectivity known to date for glycosidations with a non-participating group on O-2.
引用
收藏
页码:2251 / 2254
页数:4
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