研究论文

含醛基及叠氮基氮杂糖中间体的合成

  • 李小六 ,
  • 魏思楠 ,
  • 张宏波 ,
  • 张平竹 ,
  • 王玮 ,
  • 陈华
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  • 河北大学化学与环境科学学院 河北省化学生物学重点实验室 保定 071002

收稿日期: 2012-03-26

  修回日期: 2012-05-16

  网络出版日期: 2012-05-09

基金资助

国家自然科学基金(Nos.20972039, 21172051)、河北省自然科学基金石药集团医药联合基金(Nos.B2011201169, B2012201113)、河北省教育厅自然科学基金(Nos.ZH2011110, Y2011119)资助项目

Syntheses of Azasugar Intermediates Containing Aldehyde Group or Azide Group

  • Li Xiaoliu ,
  • Wei Sinan ,
  • Zhang Hongbo ,
  • Zhang Pingzhu ,
  • Wang Wei ,
  • Chen Hua
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  • Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002

Received date: 2012-03-26

  Revised date: 2012-05-16

  Online published: 2012-05-09

Supported by

Project supported by the National Natural Science Foundation of China (Nos.20972039, 21172051), the Medicinal Joint Funds of the Natural Science Foundation of Hebei Province and the Shijiazhuang Pharmaceuitical Group (CSPC) Foundation (Nos.B2011201169, B2012201113), and the Natural Science Foundations of Education Department of Hebei Province (Nos.ZH2011110, Y20111119)

摘要

D-甘露糖为原料,分别利用苄胺双取代和aza-Wittig反应,再经氧化和亲核取代反应,合成了带保护基的含叠氮基及醛基的五元及六元氮杂糖中间体,对相关反应条件、基团保护及反应机理等进行了探讨,并提供了一种选择性脱除三苯甲基保护基的方法.

本文引用格式

李小六 , 魏思楠 , 张宏波 , 张平竹 , 王玮 , 陈华 . 含醛基及叠氮基氮杂糖中间体的合成[J]. 有机化学, 2012 , 32(9) : 1708 -1714 . DOI: 10.6023/cjoc201203008

Abstract

Protected five and six membered azasugar intermediates containing aldehyde group or azide group were synthe-sized using D-mannose as starting material via benzyl amine disubstitution or aza-Wittig reaction, then the oxidation and SN2 substitution reactions, respectively. The studies on the reaction conditions, the protecting groups and the reaction mechanism were also carried out, providing a protocol to remove trityl (Tr) group selectively.

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