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Lewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCer

dc.contributor.authorMcDonagh, Anthony W.
dc.contributor.authorMahon, Mary F.
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2016-08-10T08:18:49Z
dc.date.issued2016-01-22
dc.identifier.citationMcDonagh, Anthony W., Mahon, Mary F., & Murphy, Paul V. (2016). Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer. Organic Letters, 18(3), 552-555. doi: 10.1021/acs.orglett.5b03591en_IE
dc.identifier.issn1523-7052
dc.identifier.urihttp://hdl.handle.net/10379/5940
dc.description.abstractThe TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid groups were attached to the anomeric Se atom. An increased amount of TiCl4 and/or higher temperature were needed to ensure completion of the reaction in some cases. Yields were higher for reactions carried out at higher dilution. The reaction was applied to the synthesis of Se-based mimics of the potent immunostimulant alpha-GalCer (KRN7000).en_IE
dc.description.sponsorshipThe research was supported by the Irish Research Council (PhD Scholarship to A.McD.) and NUI Galway (College of Science PhD scholarship to A.McD.). This publication has also emanated in part from research supported by Science Foundation Ireland (SFI, Grant Number 12/IA/1398) and is cofunded under the European Regional Development Fund under Grant Number 14/SP/2710.en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherAmerican Chemical Societyen_IE
dc.relation.ispartofOrganic Lettersen
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Ireland
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/ie/
dc.subjectChemistryen_IE
dc.subjectKiller t-cellsen_IE
dc.subjectX-ray crystallographyen_IE
dc.subjectGlucuronic aciden_IE
dc.subjectStereoselective synthesisen_IE
dc.subjectThioglycoside analogen_IE
dc.subjectEfficient synthesisen_IE
dc.subjectProtecting groupen_IE
dc.subjectGlycosyl donorsen_IE
dc.subjectFacile methoden_IE
dc.subjectC-arylationen_IE
dc.titleLewis acid induced anomerization of se-glycosides. Application to synthesis of alpha-Se-GalCeren_IE
dc.typeArticleen_IE
dc.date.updated2016-08-09T11:25:25Z
dc.identifier.doi10.1021/acs.orglett.5b03591
dc.local.publishedsourcehttp:/dx.doi.org/10.1021/acs.orglett.5b03591en_IE
dc.description.peer-reviewedpeer-reviewed
dc.contributor.funder|~|
dc.description.embargo2017-01-22
dc.internal.rssid10681264
dc.local.contactPaul Murphy, School Of Chemistry, Room 236, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedNo
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Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Ireland