title: Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines.
abstract: Protected glycosyl azides react with acyl chlorides in the presence of triphenylphosphine to afford glycosylamides in high yields, at room temperature. Starting from the beta-glycosyl azides, the reaction is highly stereoselective and occurs with retention of configuration, whereas the alpha-azido anomers display a lower stereoselectivity giving rise to alpha/beta mixtures of glycosylamides. The reaction was applied to several monosaccharidic azides and to lactosyl azide with various acyl chlorides; it was shown to be of general use for preparing 1,2-trans beta-glycosylamides.
authors.affiliation: Laboratoire de Chimie Organique II, Unité Mixte de Recherche CNRS 5622, Université de Lyon 1, Chimie Physique Electronique de Lyon, Villeurbanne, France. paul.boullanger@univ-lyon1.fr
authors.forename: P
authors.initials: P
authors.lastname: Boullanger
authors.forename: V
authors.initials: V
authors.lastname: Maunier
authors.forename: D
authors.initials: D
authors.lastname: Lafont
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002210:Caprylates; D002712:Chlorides; D006031:Glycosylation; D009943:Organophosphorus Compounds; D010084:Oxidation-Reduction; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D000577:Amides; D001386:Azides; D002210:Caprylates; D002712:Chlorides; D009943:Organophosphorus Compounds; D012997:Solvents; C061896:triphenylphosphine; C031492:octanoic acid