A CONVENIENT PREPARATION OF 2-ACETAMIDO-2,6-DIDEOXY-D-GLUCOSE, SOME OF ITS ALKYL GLYCOSIDES, AND ALLYL 2-ACETAMIDO-2,6-DIDEOXY-α-D-GALACTOPYRANOSIDE

Article abstract of DOI:10.1016/0008-6215(83)84057-9

Glycosides of 2-acetamido-2-deoxy-D-glucopyranose were treated with triphenylphosphine and N-bromosuccinimide to form the 6-bromo-6-deoxy derivatives.These, on hydrogenolysis in the presence of a palladium catalyst, yielded glycosides of 2-acetamido-2,6-dideoxy-D-glucopyranose (N-acetyl-D-quinovosamine).When the benzyl β-D-glycoside was the starting material, the product was free N-acetyl-D-quinovosamine.The allyl 6-bromo-6-deoxy-α- and -β-glycosides, after partial benzoylation, were reduced by tributyltin hydride to allyl 2-acetamido-3-O-benzoyl-2,6-dideoxy-α- and -β-glucopyranoside.The α anomer was converted into allyl 2-acetamido-2,6-dideoxy-α-D-galactopyranoside (α glycoside of N-acetyl-D-fucosamine) by successive trifluoromethylsulfonylation, displacement with cesium benzoate, and O-debenzoylation.