DIRECT SYNTHESIS OF MONO-GLYCOSYLATED CATECHOLS FROM GLYCOSYLACETATES OR IMIDATES USING BF3.OET(2) AS CATALYST-1

被引：14

作者：

MABIC, S ^{[1
]}

BENEZRA, C ^{[1
]}

LEPOITTEVIN, JP ^{[1
]}

机构：

[1] UNIV LOUIS PASTEUR,CHU,CNRS,DERMATOCHIM LAB,F-67091 STRASBOURG,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 28期

关键词：

D O I：

10.1016/0040-4039(93)88077-V

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of 3-n-alkylcatechols to the acetate or trichloroimidate derivatives of beta-D- or alpha-D- sugars (glucose, galactose. xylose, mannose and maltose) catalysed by BF3.OEt2 has been studied. Beta sugars with an equatorial acetate group at position 2 formed exclusively beta adducts with yields of 60-80%. Alpha sugars with an equatorial acetate group at position 2 formed beta adducts, while beta sugars with an axial acetate group formed alpha adducts when activated as trichloroimidates, with yields of 70-85%. Two mechanisms to explain these results are proposed.

引用

页码：4531 / 4534

页数：4

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