ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Thio-click approach to the synthesis of stable glycomimetics

László Lázár, Magdolna Csávás, Marietta Tóth, László Somsák, and Anikó Borbá

Department of Applied Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary

E-mail: borbas.aniko@pharm.unideb.hu

Abstract: 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.

Keywords: exoglycal – 3-exomethylene-furanose hydrothiolation – photocatalysis – radical – glycopeptide – glycoconjugate

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0085

Chemical Papers 69 (6) 889–895 (2015)