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A highly expeditious synthesis of a bicyclic iminosugar using the novel key step of [NMM]+[HSO4]− promoted conjugate addition and Mitsunobu reaction†
Virendra Prasad,Dhananjay Kumar,Vinod K. Tiwari
RSC Advances Pub Date : 02/26/2013 00:00:00 , DOI:10.1039/C3RA23467C
Abstract

A simple and highly facile protocol has been developed for the stereoselective synthesis of 1-deoxy-norcastanospermine from readily available D-glucose. N-Methylmorpholinium hydrogen sulphate was seen for the first time as a suitable catalyst for the facile conjugate addition of an amine to a glycosyl olefinic ester. Furthermore, the key step of this strategy is the internal reductive amination of glycosyl azetidine, obtained from glycosyl β-amino alcohol under Mitsunobu reaction conditions.

Graphical abstract: A highly expeditious synthesis of a bicyclic iminosugar using the novel key step of [NMM]+[HSO4]− promoted conjugate addition and Mitsunobu reaction
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