dc.contributor.author | Doyle, Lisa M. | |
dc.contributor.author | O'Sullivan, Shane | |
dc.contributor.author | Di Salvo, Claudia | |
dc.contributor.author | McKinney, Michelle | |
dc.contributor.author | McArdle, Patrick | |
dc.contributor.author | Murphy, Paul V. | |
dc.date.accessioned | 2018-01-09T15:30:38Z | |
dc.date.issued | 2017-10-17 | |
dc.identifier.citation | Doyle, 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.7b02760 | en_IE |
dc.identifier.issn | 1523-7052 | |
dc.identifier.uri | http://hdl.handle.net/10379/7082 | |
dc.description.abstract | 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. | en_IE |
dc.description.sponsorship | 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. | en_IE |
dc.format | application/pdf | en_IE |
dc.language.iso | en | en_IE |
dc.publisher | American Chemical Society | en_IE |
dc.relation.ispartof | Organic Letters | en |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Ireland | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/ie/ | |
dc.subject | Chemistry | en_IE |
dc.subject | Epimerizations | en_IE |
dc.subject | Glycosyl thiols | en_IE |
dc.title | Stereoselective epimerizations of glycosyl thiols | en_IE |
dc.type | Article | en_IE |
dc.date.updated | 2018-01-05T09:08:52Z | |
dc.identifier.doi | 10.1021/acs.orglett.7b02760 | |
dc.local.publishedsource | http://dx.doi.org/10.1021/acs.orglett.7b02760 | en_IE |
dc.description.peer-reviewed | peer-reviewed | |
dc.description.embargo | 2018-10-17 | |
dc.internal.rssid | 13695227 | |
dc.local.contact | Paul Murphy, School Of Chemistry, Room 236, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie | |
dc.local.copyrightchecked | No | |
dc.local.version | ACCEPTED | |
nui.item.downloads | 516 | |