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An efficient method for the synthesis of pyranoid glycals.
Chen, Heshan; Xian, Ting; Zhang, Wan; Si, Wenshuai; Luo, Xiaosheng; Zhang, Bo; Zhang, Meiyu; Wang, Zhongfu; Zhang, Jianbo.
Affiliation
  • Chen H; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Xian T; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Zhang W; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Si W; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Luo X; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Zhang B; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Zhang M; Department of Chemistry, East China Normal University, Shanghai 200241, China.
  • Wang Z; School of Life Sciences, Northwestern University, Xi'an 710069, China.
  • Zhang J; Department of Chemistry, East China Normal University, Shanghai 200241, China. Electronic address: jbzhang@chem.ecnu.edu.cn.
Carbohydr Res ; 431: 42-6, 2016 Aug 05.
Article in En | MEDLINE | ID: mdl-27295068
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Glycosides Language: En Journal: Carbohydr Res Year: 2016 Document type: Article Affiliation country:
Fulltext
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Glycosides Language: En Journal: Carbohydr Res Year: 2016 Document type: Article Affiliation country: