An efficient method for the synthesis of pyranoid glycals

Heshan Chen; Ting Xian; Wan Zhang; Wenshuai Si; Xiaosheng Luo; Bo Zhang; Meiyu Zhang; Zhongfu Wang; Jianbo Zhang

doi:10.1016/j.carres.2016.05.013

An efficient method for the synthesis of pyranoid glycals

Carbohydr Res. 2016 Aug 5:431:42-6. doi: 10.1016/j.carres.2016.05.013. Epub 2016 May 31.

Authors

Heshan Chen¹, Ting Xian¹, Wan Zhang¹, Wenshuai Si¹, Xiaosheng Luo¹, Bo Zhang¹, Meiyu Zhang¹, Zhongfu Wang², Jianbo Zhang³

Affiliations

¹ Department of Chemistry, East China Normal University, Shanghai 200241, China.
² School of Life Sciences, Northwestern University, Xi'an 710069, China.
³ Department of Chemistry, East China Normal University, Shanghai 200241, China. Electronic address: jbzhang@chem.ecnu.edu.cn.

PMID: 27295068
DOI: 10.1016/j.carres.2016.05.013

Abstract

A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was compatible with different protection patterns and conveniently scalable (86% for 45 g acetobromoglucose) which made it very applicable in organic synthesis.

Keywords: Acetonitrile; Ammonium chloride; Glycals; Glycopyranosyl bromides; Zinc.

MeSH terms

Ammonium Chloride / chemistry
Bromides / chemistry
Glycosides / chemical synthesis*
Glycosides / chemistry
Molecular Structure
Zinc / chemistry

Substances

Bromides
Glycosides
Ammonium Chloride
Zinc