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

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(英文)

作　　者：高超[1] 熊德彩[1] 王媛[1] 叶新山[1] 

机构地区：[1]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

出　　处：《Journal of Chinese Pharmaceutical Sciences》2011年第2X期139-145,共7页中国药学（英文版）

基　　金：National Natural Science Foundation of China (Grant No.20732001);Ministry of Science and Technology of China(Grant No.2009ZX09501-011).

摘　　要：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.本研究描述了利用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-Deoxy-pyranoside 2 3-Anhydrothiosugars REARRANGEMENT Carbohydrate 

分 类 号：TQ464.3[化学工程—制药化工]