Stereoselective synthesis of 2-deoxy-pyranosides via the Lewis acid-promoted rearrangement of 2,3-anhydrothiosugars

doi:10.5246/jcps.2011.02.017

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Stereoselective synthesis of 2-deoxy-pyranosides via the Lewis acid-promoted rearrangement of 2,3-anhydrothiosugars

Chao Gao, De-Cai Xiong, Yuan Wang, Xin-Shan Ye^*

State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Center, Beijing 100191, China

Received:2010-11-26 Revised:2011-02-10 Online:2011-03-15 Published:2011-03-15
Contact: Xin-Shan Ye*

Abstract

Abstract:

An efficient method for the preparation of 2-deoxy-glycopyranosides was developed by using 2,3-anhydrothioglycosides as the glycosylating agents. The reaction proceeded by the Cu(OTf)2-mediated rearrangement of 2,3-anhydrothiosugars. And high anomeric stereoselectivity was achieved. The disclosed methodology may find applications in the preparation of many biologically important 2-deoxy-glycosides.

Key words: 2-Deoxy-pyranoside, 2,3-Anhydrothiosugars, Rearrangement, Carbohydrate

CLC Number:

R916

Supporting:

Chao Gao, De-Cai Xiong, Yuan Wang, Xin-Shan Ye^* . Stereoselective synthesis of 2-deoxy-pyranosides via the Lewis acid-promoted rearrangement of 2,3-anhydrothiosugars [J]. , DOI: 10.5246/jcps.2011.02.017.

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Stereoselective synthesis of 2-deoxy-pyranosides via the Lewis acid-promoted rearrangement of 2,3-anhydrothiosugars

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