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GLYCOSYL TRANSFER BY ISOPROPENYL GLYCOSIDES - TRISACCHARIDE SYNTHESIS IN ONE-POT BY SELECTIVE COUPLING OF ISOPROPENYL AND N-PENTENYL GLUCOPYRANOSIDES

被引：64
作者：
CHENAULT, HK
CASTRO, A
机构：
[1] Department of Chemistry and Biochemistry, University of Delaware, Newark
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 49期
关键词：
D O I：
10.1016/0040-4039(94)88449-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
O-Isopropenyl glycosides bearing ester protecting groups are activated as glycosyl donors by a variety of electrophiles. Diastereomerically pure beta-glycoside products are formed in good yields. Selective activation of O-isopropenyl 2,3,4,6-tetra-O-pivaloyl-beta-glucopyranoside in the presence of O-pent-4-enyl 2,3,4,6-tetra-O-benzyl-beta-glucopyranoside allows two successive glycosyl couplings to be performed in a single pot to give trisaccharide in 25% yield.
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页码：9145 / 9148
页数：4
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