Rhenium(V)-catalyzed synthesis of 1,1'-2-deoxy thioglycosides

Xiang Zhao; Bin Wu; Penghua Shu; Lingkui Meng; Jing Zeng; Qian Wan

doi:10.1016/j.carres.2021.108415

Rhenium(V)-catalyzed synthesis of 1,1'-2-deoxy thioglycosides

Carbohydr Res. 2021 Oct:508:108415. doi: 10.1016/j.carres.2021.108415. Epub 2021 Jul 30.

Authors

Xiang Zhao¹, Bin Wu¹, Penghua Shu¹, Lingkui Meng¹, Jing Zeng¹, Qian Wan²

Affiliations

¹ Hubei 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.
² Hubei 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; Institute of Brain Research, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei, 430030, China. Electronic address: wanqian@hust.edu.cn.

PMID: 34358864
DOI: 10.1016/j.carres.2021.108415

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.

Keywords: 1,1′-disaccharide; 2-deoxy glycoside; Rhenium catalysis; Thioglycoside.

MeSH terms

Catalysis
Chemistry Techniques, Synthetic
Glycosylation
Rhenium* / chemistry
Thioglycosides* / chemical synthesis
Thioglycosides* / chemistry

Substances

Thioglycosides
Rhenium