利用路易斯酸介导的2,3-环氧吡喃糖硫苷的重排反应立体选择性合成2-脱氧吡喃糖苷

doi:10.5246/jcps.2011.02.017

利用路易斯酸介导的2,3-环氧吡喃糖硫苷的重排反应立体选择性合成2-脱氧吡喃糖苷

高超, 熊德彩, 王媛, 叶新山^*

北京大学医学部天然药物及仿生药物国家重点实验室北京 100191

收稿日期:2010-11-26 修回日期:2011-02-10 出版日期:2011-03-15 发布日期:2011-03-15
通讯作者: 叶新山*

Stereoselective synthesis of 2-deoxy-pyranosides via the Lewis acid-promoted rearrangement of 2,3-anhydrothiosugars

Chao Gao, De-Cai Xiong, Yuan Wang, Xin-Shan Ye^*

State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Center, Beijing 100191, China

Received:2010-11-26 Revised:2011-02-10 Online:2011-03-15 Published:2011-03-15
Contact: Xin-Shan Ye*

摘要/Abstract

摘要： 用2,3-环氧吡喃糖硫苷作为糖基化试剂制备2-脱氧吡喃糖苷的方法。在Cu(OTf)2 的介导下, 2,3-环氧吡喃糖硫苷与糖基受体发生重排并进行糖基化反应生成2-硫代-2-脱氧糖苷。该方法立体选择性高, 可能会在制备具有重要生物活性的2-脱氧糖苷方面有广泛的应用。

关键词: 2-脱氧吡喃糖苷, 2,3-环氧吡喃糖硫苷, 重排, 碳水化合物

Abstract:

An efficient method for the preparation of 2-deoxy-glycopyranosides was developed by using 2,3-anhydrothioglycosides as the glycosylating agents. The reaction proceeded by the Cu(OTf)2-mediated rearrangement of 2,3-anhydrothiosugars. And high anomeric stereoselectivity was achieved. The disclosed methodology may find applications in the preparation of many biologically important 2-deoxy-glycosides.

Key words: 2-Deoxy-pyranoside, 2,3-Anhydrothiosugars, Rearrangement, Carbohydrate

中图分类号:

R916

Supporting:

Foundation items: National Natural Science Foundation of China (Grant No. 20732001) and Ministry of Science and Technology of China (Grant No. 2009ZX09501-011).
^*Corresponding author. Tel.: 86-10-62014949

高超, 熊德彩, 王媛, 叶新山^*. 利用路易斯酸介导的2,3-环氧吡喃糖硫苷的重排反应立体选择性合成2-脱氧吡喃糖苷[J]. , DOI: 10.5246/jcps.2011.02.017.

Chao Gao, De-Cai Xiong, Yuan Wang, Xin-Shan Ye^* . Stereoselective synthesis of 2-deoxy-pyranosides via the Lewis acid-promoted rearrangement of 2,3-anhydrothiosugars [J]. , DOI: 10.5246/jcps.2011.02.017.

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