機能性官能基を利用した2-チオシアル酸誘導体の新規グリコシル化

抄録

N-Acetylneuraminic acid (Neu5Ac), sialic acid and its various analogs play essential roles in a variety of biochemical and biological processes. The development of an efficient method of O-sialylation has been a challenging task in the field of sialic acid chemistry. The reaction of 2-thiosialic acids with alcohols was activated by silver triflate or cupric triflate as promoters to give the corresponding O-glycosides in moderate yields. Herein, we report a novel procedure for the synthesis of thiazolyl, pyridinyl, pyrimidinyl, benzothiazolyl and benzoxazoyl 2-thiosialic acids having substituted imidoyl groups as glycosyl donors and their application to the glycosylation reaction.

Scheme 1