Odorless benzenethiols in synthesis of thioglycosides and its application for glycosylation reactions.

p-Octyloxybenzenethiol (2) was synthesized as a new odorless benzenethiol. Moreover, preparation of thioglycosides using 2 and their application for glycosylation reactions were attempted. As a result, it was found that the thioglycosides were as excellent glycosyl donors as 4-dodecylphenyl 1-thio-glycosides, which were previously reported by our group, and more useful than the previous donors in terms of fine chemistry in glycosylation reaction activated with silver triflate and N-iodosuccinimide (NIS). In addition, this method was applicable to the sialylation with NIS and triflic acid. All procedures from the preparation of thioglycosides to the glycosylation reaction could be attained completely under conditions where no malodor was generated.