UNSATURATED CARBOHYDRATES .30. SYNTHESES AND REACTIONS OF SATURATED AND 2,3-UNSATURATED VINYL AND 1'-SUBSTITUTED-VINYL GLYCOSIDES

被引：29

作者：

DERAADT, A

FERRIER, RJ

机构：

[1] Department of Chemistry, Victoria University of Wellington, Wellington

来源：

CARBOHYDRATE RESEARCH | 1991年 / 216卷

关键词：

D O I：

10.1016/0008-6215(92)84153-J

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Reaction of tetra-O-acetyl-alpha-D-glucopyranosyl bromide with bis(acylmethyl)mercurys [Hg (CH2COR)2] afforded acetylated vinyl [by use of bis(formylmethyl)mercury] or 1'-substituted-vinyl beta-D-glucopyranosides 11-13 in high yields. When used together with phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-alpha-D-erythro-hex-2-enopyranoside, these reagents gave analogous vinyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 20-23 which, on treatment with Lewis acids, isomerised to the corresponding C-glycosyl compounds, i.e., (4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)acetaldehyde (24,25) or the corresponding glycosylated methyl ketones 26, 27. A new route to C-3-branched glycals involves treatment of the above thioglycoside or the unsaturated vinyl glycosides with bis(benzoylmethyl)-mercury.

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页码：93 / 107

页数：15

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