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Free-radical hydrothiolation of glycals: a thiol-ene-based synthesis of S-disaccharides |
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| Authors: | Samuele Staderini Angela Chambery Alberto Marra Alessandro Dondoni |
| Institution: | 1. Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, 44100 Ferrara, Italy;2. Dipartimento di Scienze della Vita, II Università di Napoli, Via Vivaldi 43, 81100 Caserta, Italy |
| Abstract: | A method for the synthesis of a new family of 1-deoxy S-disaccharides has been established via free-radical hydrothiolation of glycals by sugar thiols (thiol-ene coupling). The photoinduced coupling between four tri-O-acetyl-d-glycals and three different sugar thiols reveals that the reaction efficiency and stereoselectivity are highly dependent on the stereochemistry of the OAc groups at C3 and C4 of the glycal. |
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