SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS-III - A FACILE CHEMICAL SYNTHESIS OF 6-O-ACYL-D-GLYCOPYRANOSES AND METHYL-6-O-ACYL-D-GLYCOPYRANOSIDES

被引：20

作者：

BACZKO, K ^{[1
]}

PLUSQUELLEC, D ^{[1
]}

机构：

[1] ECOLE NATL SUPER CHIM RENNES,CNRS,CHIM ORGAN & SUBST NAT LAB,AVE GEN LECLERC,F-35700 RENNES,FRANCE

来源：

TETRAHEDRON | 1991年 / 47卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)80906-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective acylation of non protected glycopyranosides was performed using 3-acylthiazolidine-2-thiones 1 and the novel 3-acyl-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 2 as the acylating reagents, yielding 6-O-acylated derivatives in high yields. Acylation of free alpha-D-glucose and alpha-D-galactose using the same conditions lead to the 6-O-acylglycoses. This reaction is compared with our previous synthesis of 1-O-acyl-beta-D-glucoses from beta-D-glucose.

引用

页码：3817 / 3828

页数：12

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