Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines.
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.
Boullanger
P
P
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
Maunier
V
V
Lafont
D
D
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
D000577:Amides; D001386:Azides; D002210:Caprylates; D002712:Chlorides; D009943:Organophosphorus Compounds; D012997:Solvents; C061896:triphenylphosphine; C031492:octanoic acid