title: Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under Lewis acidic conditions.
abstract: N-acetyl 4-O,5-N-oxazolidinone protected sialyl phosphates of either anomeric configuration are excellent donors for the formation of α-S-sialosides at -78 °C in dichloromethane with primary, secondary, and tertiary thiols including galactose 3-, 4-, and 6-thiols. The reactions, which proceed under typical Lewis acid promoted glycosylation conditions, are highly α-selective and do not suffer from competing elimination of the phosphate.
authors: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
authors: Amandine
authors: A
authors: Noel
authors: Bernard
authors: B
authors: Delpech
authors: David
authors: D
authors: Crich
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005690:Galactose / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D019158:N-Acetylneuraminic Acid / Q000737:chemistry*; D012794:Sialic Acids / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D006027:Glycosides; D058116:Lewis Acids; D012794:Sialic Acids; D013438:Sulfhydryl Compounds; D019158:N-Acetylneuraminic Acid; D005690:Galactose