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dc.contributor.authorDoyle, Lisa M.
dc.contributor.authorO'Sullivan, Shane
dc.contributor.authorDi Salvo, Claudia
dc.contributor.authorMcKinney, Michelle
dc.contributor.authorMcArdle, Patrick
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2018-01-09T15:30:38Z
dc.date.issued2017-10-17
dc.identifier.citationDoyle, Lisa M., O’Sullivan, Shane, Di Salvo, Claudia, McKinney, Michelle, McArdle, Patrick, & Murphy, Paul V. (2017). Stereoselective Epimerizations of Glycosyl Thiols. Organic Letters, 19(21), 5802-5805. doi: 10.1021/acs.orglett.7b02760en_IE
dc.identifier.issn1523-7052
dc.identifier.urihttp://hdl.handle.net/10379/7082
dc.description.abstractGlycosyl 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.en_IE
dc.description.sponsorshipThe 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.en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherAmerican Chemical Societyen_IE
dc.relation.ispartofOrganic Lettersen
dc.subjectChemistryen_IE
dc.subjectEpimerizationsen_IE
dc.subjectGlycosyl thiolsen_IE
dc.titleStereoselective epimerizations of glycosyl thiolsen_IE
dc.typeArticleen_IE
dc.date.updated2018-01-05T09:08:52Z
dc.identifier.doi10.1021/acs.orglett.7b02760
dc.local.publishedsourcehttp://dx.doi.org/10.1021/acs.orglett.7b02760en_IE
dc.description.peer-reviewedpeer-reviewed
dc.description.embargo2018-10-17
dc.internal.rssid13695227
dc.local.contactPaul Murphy, School Of Chemistry, Room 236, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedNo
dc.local.versionACCEPTED
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