ARYLBIS(ARYLTHIO)SULFONIUM SALTS AS REAGENTS FOR THE SYNTHESIS OF 2-DEOXY-BETA-GLYCOSIDES

被引：86

作者：

GREWAL, G ^{[1
]}

KAILA, N ^{[1
]}

FRANCK, RW ^{[1
]}

机构：

[1] CUNY HUNTER COLL,DEPT CHEM,695 PK AVE,NEW YORK,NY 10021

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 07期

关键词：

D O I：

10.1021/jo00033a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title sulfonium salts undergo electrophilic addition to glycals in the presence of alcohols to form principally beta-glycosides. A substituent effect study has shown that the reagent with a p-tolylthio group is the most face-selective. By variation of the alcohol nucleophile, it has been shown that face selectivity is also dependent on the structure of the nucleophile. One instance of double diastereodifferentiation was uncovered when the racemic alcohol 23.5 was used in a reaction with tribenzyl glucal 22.1. The effect of glycal substitution on the face selectivity has led to the postulation of a heretofore unrecognized and still unexplained stereoelectronic effect.

引用

页码：2084 / 2092

页数：9

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