Rhenium(V)-catalyzed synthesis of 1,1'-2-deoxy thioglycosides
Xiang Zhao1, Bin Wu1, Penghua Shu1
1Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei, 430030, China.
Abstract:
As stable glycomimetics, thioglycosides are important tools for the investigation of biological processes and discovery of new drugs. In this note, we report a ReOCl3(SMe2)(OPPh3) catalyzed coupling reaction between β-glycosyl thiols (1-thio sugars) and glycals for the preparation of 1,1'-α,β-2-deoxy thioglycosides, which are glycomimetics of natural trehalose and 2-deoxy glycosides. Furthermore, an S-linked trisaccharide was successfully obtained by successive employment of the Re(V) catalyzed thioglycosylation protocol.
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