Modifications at the 6-<i>O</i>-position of 1-deoxynojirimycin: facile and efficient synthesis of 6-<i>O</i>-alkylated-<i>N</i>-octyl-1-deoxynojirimycin derivatives

2017-12-04T18:02:05Z (GMT) by Mehwish Iftikhar Zhijie Fang
<p>A straightforward synthesis of <i>N</i>-alkylated 1-deoxynojirimycin derivatives modified at the 6-<i>O</i>-position has been described. The key intermediate in the synthesis of target compounds was 2,3,4-tri-<i>O</i>-benzyl-1,5-dideoxy-1,5-imino-D-glucitol, which was prepared from 2,3,4,6-tetra-<i>O</i>-benzyl-1,5-dideoxy-1,5-imino-D-glucitol. Optimal conditions have been established for the synthesis of the key intermediate by varying reaction parameters. Reductive amination and subsequent alkylation of the 6-<i>O</i>-position followed by hydrogenolysis were the main reaction steps, which gave target compounds 6-<i>O</i>-ethyl-<i>N</i>-octyl-1,5-dideoxy-1,5-imino-D-glucitol and 6-<i>O</i>-butyl-<i>N</i>-octyl-1,5-dideoxy-1,5-imino-D-glucitol. This synthetic route is flexible and can be useful for the synthesis of other lipophilic iminosugar derivatives.</p>