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Stereoselective epimerizations of glycosyl thiols
Doyle, Lisa M.; O'Sullivan, Shane; Di Salvo, Claudia; McKinney, Michelle; McArdle, Patrick; Murphy, Paul V.
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation. The authors thank Science Foundation Ireland for an IvP award (Grant Number 12/IA/1398) cofunded by the European Regional Development Fund (Grant Number 14/ SP/2710). The Irish Research Council can also be thanked for a scholarship award to M. McKinney. 2018-10-17
Keyword(s): Chemistry; Epimerizations; Glycosyl thiols
Publication Date:
2018
Type: Journal article
Peer-Reviewed: Yes
Language(s): English
Institution: NUI Galway
Publisher(s): American Chemical Society
File Format(s): application/pdf
First Indexed: 2018-02-28 06:20:11 Last Updated: 2018-02-28 06:20:11