Thio-click approach to the synthesis of stable glycomimetics

Lázár, László and Csávás, Magdolna and Tóth, Marietta and Somsák, László and Borbás, Anikó (2015) Thio-click approach to the synthesis of stable glycomimetics. Chemical Papers, 69 (6). pp. 889-895. ISSN 0366-6352, ESSN: 1336-9075


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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.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Dr L Lázár
Date Deposited: 09 Sep 2015 13:04
Last Modified: 03 Mar 2016 05:47

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