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

doi:10.5246/jcps.2011.06.070

Abstract

Abstract:

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

CLC Number:

R916.42

Supporting:

Sheng Sun, Qing Ma, Xiang-Bao Meng, Qing Li, Shu-Chun Li, He-Qing Huang, Zhong-Jun Li^* . The β-directing effect of ionic liquid in mannopyranosylation: a potential access to stereoselective construction of the 1,2-cis-β-D-mannopyranosyl linkage[J]. , DOI: 10.5246/jcps.2011.06.070.

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