SYNTHESIS OF C-GLYCOSIDES - USE OF AN ARSENIC DERIVATIVE

被引：12

作者：

DHEILLY, L ^{[1
]}

LIEVRE, C ^{[1
]}

FRECHOU, C ^{[1
]}

DEMAILLY, G ^{[1
]}

机构：

[1] FAC SCI AMIENS,CHIM ORGAN LAB,VALORISAT GLUCIDES GRP,33 RUE ST LEU,F-80039 AMIENS,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 37期

关键词：

(CARBOMETHOXYMETHYL)TRIPHENYLARSONIUM YLIDE; ARSONIUM SALT; ALDOSES; E-OLEFINS; C-GLYCOSYL COMPOUNDS;

D O I：

10.1016/S0040-4039(00)73808-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of arsenic ylides with pyranose and furanose carbohydrates mainly leads to E-olefinic derivatives. Cyclisation of the olefinic derivatives obtained from 2,3,4,6-tetra-O-benzyl-D-glucose and D-galactose, promoted by ZnBr2, gives C-glycosyl compounds with high stereoselectivity. One the other hand, reaction of the corresponding arsonium salt, in presence of zinc, with a furanose derivative gives directly and stereosectively the beta-C-glycosyl compound.

引用

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页码：5895 / 5898

页数：4

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