title: Access to L- and D-iminosugar C-glycosides from a D-gluco-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.
authors.affiliation: Institut de Chimie des Milieux et des Matériaux de Poitiers (IC2MP), UMR CNRS 7285, Université de Poitiers, Equipe Chimie Organique, Bioorganique et Supramoléculaire 4 avenue Michel Brunet, 86022 Poitiers cedex, France.
authors.forename: Martine
authors.initials: M
authors.lastname: Mondon
authors.forename: Nathalie
authors.initials: N
authors.lastname: Fontelle
authors.forename: Jérôme
authors.initials: J
authors.lastname: Désiré
authors.forename: Frédéric
authors.initials: F
authors.lastname: Lecornué
authors.forename: Jérôme
authors.initials: J
authors.lastname: Guillard
authors.forename: Jérôme
authors.initials: J
authors.lastname: Marrot
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
mesh_terms: D000478:Alkylation; D001381:Azepines / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D050111:Imino Sugars / Q000737:chemistry*; D007536:Isomerism; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001381:Azepines; D001386:Azides; D006027:Glycosides; D050111:Imino Sugars; D007783:Lactones