Conversion of N-acetylneuraminic acid glycosyl chloride into dibenzyl glycosyl phosphate:O-glycosylation in the absence of a promoter

摘要

Readily accessible N-acetylneuraminic acid(Neu5Ac)glycosyl chloride,which was regarded to be a poor glycosyl donor,was shown to react with dibenzyl phosphoric acid salts in the absence of glycosylation promoters to give the corresponding beta-Neu5Ac dibenzyl glycosyl phosphate in high yield.The development of new efficient procedures for the synthesis of oligosaccharides containing sialic acid residues and,in particular,A^-acetyhieuraminic acid(NeuSAc)residue,which are responsible for various immunological,neurobiological,oncological,and other biological processes,1 is an important problem of modern synthetic carbohydrate chemistry.