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The β-directing effect of ionic liquid in mannopyranosylation: a potential access to stereoselective construction of the 1,2-cis-β-D-mannopyranosyl linkage

Sheng Sun, Qing Ma, Xiang-Bao Meng, Qing Li, Shu-Chun Li, He-Qing Huang, Zhong-Jun Li*   

  1. State Key Laboratory of Natural and Biomimetic Drugs; Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China
  • Received:2011-06-28 Revised:2011-09-20 Online:2011-11-15 Published:2011-11-15
  • Contact: Zhong-Jun Li*


We report a novel β-directing effect of imidazolium based ionic liquid, which was observed when we conducted the glycosylation of a 6-O-acetyl-2,3,4-tri-O-benzyl-mannose trichloroacetimidate donor with a modified ionic liquid support acceptor. The mechanism was investigated and a hypothesis was proposed. After optimization of the reaction conditions, an innovative method for the selective construction of 1,2-cis-β-D-mannopyranosyl linkage was developed.

Key words: Ionic liquid supported strategy, Glycosylation, Stereoselectivity

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