一种通用的 N-烷基化 1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇和 1,4-二脱氧-1,4-亚氨基-L-木酮糖醇的方法。

A versatile approach to N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitols and 1,4-dideoxy-1,4-imino-L-xylitols.

机构信息

State Key Laboratory of Natural and Biomimetic Drugs and School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China.

出版信息

J Org Chem. 2011 Apr 1;76(7):2001-9. doi: 10.1021/jo1020322. Epub 2011 Mar 4.

DOI:10.1021/jo1020322

PMID:21375224

Abstract

A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from sucrose. The key intermediates were prepared by a diastereospecific tandem reaction which facilitated the introduction of various substituents on the nitrogen atom of the iminosugars.

摘要

本文描述了一种通用且简洁的 N-烷基化 1,4-二脱氧-1,4-亚氨基-D-阿拉伯糖醇和 1,4-二脱氧-1,4-亚氨基-L-木糖醇衍生物的合成方法。这些化合物是使用伪半缩酮内酰胺作为关键中间体制备的，而这些中间体又是由蔗糖制备的。关键中间体是通过立体选择性串联反应制备的，该反应有利于在亚氨基糖的氮原子上引入各种取代基。