Access to <scp>l</scp>- and <scp>d</scp>-Iminosugar C-Glycosides from a <scp>d</scp>-<i>gluco</i>-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

Abstract

A flexible synthetic access to six-membered L- and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.