Synlett 2014; 25(3): 308-312
DOI: 10.1055/s-0033-1340309
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© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of S-Linked 2-Deoxy Sugars

Kedar N. Baryal
Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606, USA   Fax: +1(419)5304033   Email: Jianglong.Zhu@utoledo.edu
,
Jianglong Zhu*
Department of Chemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606, USA   Fax: +1(419)5304033   Email: Jianglong.Zhu@utoledo.edu
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Further Information

Publication History

Received: 05 October 2013

Accepted after revision: 28 October 2013

Publication Date:
06 December 2013 (online)

Abstract

Stereoselective synthesis of S-linked 2-deoxysugars, potentially nonhydrolyzable mimics of naturally occurring O-linked 2-deoxy sugars, remains a challenge due to the absence of a directing group at C2. This article describes recent efforts in the stereo­selective synthesis of S-linked 2-deoxy sugars, including our approach which involves sulfenylation of stereochemically defined 2-deoxyglycosyl lithiums with asymmetric sugar-derived disulfides.

 
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