A highly efficient deprotection of the 2,2,2-trichloroethyl group at the anomeric oxygen of carbohydrates

Jianbo Zhang; Jie Fu; Wenshuai Si; Xiaohu Wang; Zhongfu Wang; Jie Tang

doi:10.1016/j.carres.2011.08.007

A highly efficient deprotection of the 2,2,2-trichloroethyl group at the anomeric oxygen of carbohydrates

Carbohydr Res. 2011 Oct 18;346(14):2290-3. doi: 10.1016/j.carres.2011.08.007. Epub 2011 Aug 16.

Authors

Jianbo Zhang¹, Jie Fu, Wenshuai Si, Xiaohu Wang, Zhongfu Wang, Jie Tang

Affiliation

¹ Department of Chemistry, East China Normal University, Shanghai 200062, China. jbzhang@chem.ecnu.edu.cn

PMID: 21889124
DOI: 10.1016/j.carres.2011.08.007

Abstract

Commercially available zinc dust in the presence of ammonium chloride in acetonitrile at reflux removes the 2,2,2-trichloroethyl (TCE) group at anomeric centers with excellent yields (>95%) in short reaction times. This present method is easily implemented on substrates containing acyl and benzyl groups and large-scale reactions also proceed in high yield.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrates / chemistry*
Isomerism
Kinetics
Oxygen / chemistry*

Substances

Carbohydrates
Oxygen