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

Martine Mondon (1) , Nathalie Fontelle (1) , Jérôme Désiré (1) , Frédéric Lecornué (1) , Jérôme Guillard (1) , Jérôme Marrot (2) , Yves Blériot (1)

1 OrgaSynth - Synthèse organique [E5 – IC2MP équipe 5]
2 ILV - Institut Lavoisier de Versailles

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.

Domaines: Chimie organique; Autre

Martine Mondon, Nathalie Fontelle, Jérôme Désiré, Frédéric Lecornué, Jérôme Guillard, et al.. Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy.. Organic Letters, 2012, 14 (3), pp.870-3. ⟨10.1021/ol203385w⟩. ⟨hal-00669930⟩