Application of novel glycosides prepared with odorless benzenethiols in glycosylation reaction

p-Dodecylbenzenethiol (1) and p-octyloxybenzenethiol (2) were synthesized as new odorless benzenethiols. Moreover, preparation of novel 1-thioglycosides using 1 and 2 as well as their application for glycosylation reactions was performed. As a result, it was found that these 1-thio-glycosides were excellent glycosyl donors, and especially 2-thio-sialoside prepared from 1 and 2 afforded the best result to date in terms of alpha- and beta-selectivity in the sialylation where only the single C-3 hydroxyl group of acceptor D-galactopyranoside was free. All procedures from the preparation of thioglycosides to glycosylation reaction were attainable under completely odorless conditions.