Stereoselective synthesis of azasugars by electrochemical oxidation

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• 作者：Furukubo ; Shigeru ; Moriyama ; Noriaki ; Onomura ; Osamu ; Matsumura ; Yoshihiro
• 关键词：Azasugar ; Electrochemical oxidation ; Stereoselective ; Acetoxylation
• 刊名：Tetrahedron Letters
• 出版年：2004
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：October 25, 2004
• 卷：45
• 期：44
• 页码：8177-8181
• 文件大小：299 K

摘要

A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine.