离子液体在甘露糖苷化过程中的β导向性: 一种具有选择性构建1,2-顺式-β-D-甘露糖连接潜力的新方法

doi:10.5246/jcps.2011.06.070

离子液体在甘露糖苷化过程中的β导向性: 一种具有选择性构建1,2-顺式-β-D-甘露糖连接潜力的新方法

孙晟, 马庆, 孟祥豹, 李庆, 李树春, 黄河清, 李中军^*

北京大学医学部天然药物及仿生药物国家重点实验室; 药学院化学生物学系, 北京 100191

收稿日期:2011-06-28 修回日期:2011-09-20 出版日期:2011-11-15 发布日期:2011-11-15
通讯作者: 李中军*

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^*

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*

摘要/Abstract

摘要：

首次报道了甲基咪唑型离子液体在进行6-O-乙酰基-2,3,4-O-三-苄基-甘露糖三氯乙酰亚胺酯供体与离子液体载体的糖基化过程中的β导向性, 并对该反应进行了深入研究, 探讨了出现该现象的潜在机理。在对反应条件进行了优化之后, 我们发展了一种选择性构建1,2-顺式-β-D-甘露糖连接的全新方法。

关键词: 离子液体负载策略, 糖基化, 立体选择性

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

中图分类号:

R916.42

Supporting:

Foundation items: National Natural Science Foundation of China (Grant No. 20732001) and the State New Drug Innovation (the Ministry of Science and Technology of China, Grant No. 2009ZX09501-011).
^*Corresponding author. Tel.: 86-10-82801714

孙晟, 马庆, 孟祥豹, 李庆, 李树春, 黄河清, 李中军^*. 离子液体在甘露糖苷化过程中的β导向性: 一种具有选择性构建1,2-顺式-β-D-甘露糖连接潜力的新方法[J]. , DOI: 10.5246/jcps.2011.06.070.

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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