A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen

SS Chang, CC Lin, YK Li, KKT Mong

Index: Chang, Shih-Sheng; Lin, Chun-Cheng; Li, Yaw-Kuen; Mong, Kwok-Kong Tony Carbohydrate Research, 2009 , vol. 344, # 4 p. 432 - 438

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Citation Number: 14

Abstract

A practical and efficient α-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L- fucosyl and 2-azido-2-deoxy-d-galatosaminyl imidates, with which exclusive α-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl α-T-antigen.