An efficient method for the synthesis of pyranoid glycals.
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.
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Heshan
H
Chen
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Ting
T
Xian
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Wan
W
Zhang
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Wenshuai
W
Si
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Xiaosheng
X
Luo
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Bo
B
Zhang
Department of Chemistry, East China Normal University, Shanghai 200241, China.
Meiyu
M
Zhang
School of Life Sciences, Northwestern University, Xi'an 710069, China.
Zhongfu
Z
Wang
Department of Chemistry, East China Normal University, Shanghai 200241, China. Electronic address: jbzhang@chem.ecnu.edu.cn.
Jianbo
J
Zhang
D000643:Ammonium Chloride / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D015032:Zinc / Q000737:chemistry
D001965:Bromides; D006027:Glycosides; D000643:Ammonium Chloride; D015032:Zinc
Acetonitrile; Ammonium chloride; Glycals; Glycopyranosyl bromides; Zinc