FUNCTIONALIZED C-GLYCOSYL COMPOUNDS .3. REACTION OF TERTIARY NUCLEOPHILES WITH UNSATURATED CARBOHYDRATES - MECHANISM OF THE ANOMERIZATION

被引：14

作者：

CHAGUIR, B ^{[1
]}

BRAKTA, M ^{[1
]}

BOLITT, V ^{[1
]}

LHOSTE, P ^{[1
]}

SINOU, D ^{[1
]}

机构：

[1] UNIV LYON 1,ECOLE SUPER CHIM IND LYON,CNRS,SYNTH ASYMETR LAB,F-69622 VILLEURBANNE,FRANCE

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1992年 / 11卷 / 05期

关键词：

D O I：

10.1080/07328309208016152

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：

Phenyl 2,3-dideoxy-4,6-di-O-benzyl-D-erythro-hex-2-enopyranoside 1-alpha (or 1-beta) is alkylated regio- and stereospecifically at the anomeric center by stabilized tertiary nucleophiles in the presence of Pd(0) as a catalyst, leading to the C-glycoside of alpha- (or beta-) configuration. The observed loss of stereoselectivity using secondary stabilized nucleophiles is mainly due to a retro Michael reaction. The assignment of the alpha- ( or beta-) configuration at the anomeric center was accomplished using C-13 NMR and NOE experiments.

引用

页码：609 / 625

页数：17

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