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Synlett 2014; 25(3): 308-312
DOI: 10.1055/s-0033-1340309
DOI: 10.1055/s-0033-1340309
synpacts
Stereoselective Synthesis of S-Linked 2-Deoxy Sugars
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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For reviews on synthetic studies of 2-deoxy sugars, see:
For previous preparation of sulfides via reactions between lithium carbanions with disulfides, see: