An efficient method for the synthesis of pyranoid glycals

作者:Chen, Heshan; Xian, Ting; Zhang, Wan; Si, Wenshuai; Luo, Xiaosheng; Zhang, Bo; Zhang, Meiyu; Wang, Zhongfu; Zhang, Jianbo*
来源:Carbohydrate Research, 2016, 431: 42-46.
DOI:10.1016/j.carres.2016.05.013

摘要

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 degrees 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 aceto-bromoglucose) which made it very applicable in organic synthesis.