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Licensed Unlicensed Requires Authentication Published by De Gruyter March 19, 2015

Thio-click approach to the synthesis of stable glycomimetics

  • László Lázár , Magdolna Csávás , Marietta Tóth , László Somsák and Anikó Borbás EMAIL logo
From the journal Chemical Papers


Carbon-sulfur-bridged glycomimetics were prepared by free radical hydrothiolation of the exocyclic double bond of unsaturated sugars. Reaction between benzoyl-substituted pyranoid-exoglycal and a range of thiols including peptide, 1-thioglycerol and 1-thiosugar derivatives gave β-Dconfigured carbon-sulfur-linked glycoconjugates with full stereoselectivity. Addition of a panel of thiols to a 3-exomethylene-glucofuranose derivative also proceeded in a stereoselective manner and afforded a series of D-allo-configured 3-deoxy-3-C-S-bridged glycoconjugates.


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Received: 2014-9-25
Revised: 2014-11-18
Accepted: 2014-11-24
Published Online: 2015-3-19
Published in Print: 2015-6-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

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