One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides

被引：10

作者：

Lohman, GJS ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

[1] MIT, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 19期

关键词：

D O I：

10.1021/jo034386i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described is a general method for the conversion of glycals to the corresponding 1,2-cis-isopropylidene-alpha-glycosides. Epoxidation of glycals with dimethyldioxirane followed by ZnCl2-catalyzed addition of acetone converted a variety of protected glycals into 1,2-cis-isopropylidene-alpha-glycosides in good yield. The reaction is compatible with a range of protecting groups, including esters, benzyl ethers, and silyl ethers, as well as free hydroxyl groups. This method has been applied to develop a synthesis of protected glucuronic acid 1, a key intermediate in the synthesis of glycosaminoglycans. Compound 1 was produced in seven steps and 32% overall yield.

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页码：7541 / 7543

页数：3

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