Organic Letters 2004-04-29

A new reaction for the direct conversion of 4-azido-4-deoxy-D-galactoside into a 4-deoxy-D-erythro-hexos-3-ulose.

Jie Xue, Jian Wu, Zhongwu Guo

Index: Org. Lett. 6 , 1365-1368, (2004)

Full Text: HTML

Abstract

[reaction: see text] A new one-step reaction has been developed for converting 4-azido-4-deoxy-d-galactoside into 4-deoxy-d-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the phosphite intermediate and a tetrazole-catalyzed elimination reaction of the resultant phosphorimidate. Tetrazole appears to be playing a unique role by acting as a bifunctional catalyst to facilitate the elimination reaction.