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Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation

dc.contributor.authorFarrell, Mark P.
dc.contributor.authorDoyle, Lisa M.
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2019-05-24T11:27:36Z
dc.date.issued2018-05-26
dc.identifier.citationFarrell, Mark P., Doyle, Lisa M., & Murphy, Paul V. (2018). Influence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisation. Tetrahedron Letters, 59(28), 2726-2731. doi: https://doi.org/10.1016/j.tetlet.2018.05.076en_IE
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/10379/15195
dc.description.abstractLewis acid promoted anomerisation has potential in O- or S-glycoside synthesis. Herein, the anomerisation kinetics of thirty-one β-d-glucopyranosides was determined to determine how particular acyl protecting groups and their location influence reactivity towards a Lewis acid promoted reaction. The replacement of acetyl groups with benzoyl groups led to reduced reactivity when located at O-3, O-4 and O-6. However a reactivity increase was observed when the acetyl group was replaced by a benzoyl group at O-2. The 2,3,4,6-tetra-O-(4-methoxy)benzoate had an⠯⠼2-fold increase in rate when compared to the tetrabenzoate.en_IE
dc.description.sponsorshipThis publication has partly emanated from research supported by Science Foundation Ireland (SFI, grant number 12/IA/1398) and is co-funded under the European Regional Development Fund under Grant Number 14/SP/2710. The authors thank the Irish Research Council and Roche Ireland Ltd for an Enterprise Partnership postgraduate scholarship to MPF.en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherElsevieren_IE
dc.relation.ispartofTetrahedron Lettersen
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Ireland
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/3.0/ie/
dc.subjectCarbohydratesen_IE
dc.subjectAnomerisationen_IE
dc.subjectGlycosideen_IE
dc.subjectLewis aciden_IE
dc.subjectProtecting groupsen_IE
dc.subjectReactivityen_IE
dc.titleInfluence of acyl groups on glucopyranoside reactivity in Lewis acid promoted anomerisationen_IE
dc.typeArticleen_IE
dc.date.updated2019-05-23T14:16:45Z
dc.identifier.doi10.1016/j.tetlet.2018.05.076
dc.local.publishedsourcehttps://doi.org/10.1016/j.tetlet.2018.05.076en_IE
dc.description.peer-reviewedpeer-reviewed
dc.contributor.funderScience Foundation Irelanden_IE
dc.contributor.funderEuropean Regional Development Funden_IE
dc.contributor.funderIrish Research Councilen_IE
dc.contributor.funderRoche Ireland Ltden_IE
dc.description.embargo2020-05-26
dc.internal.rssid16255768
dc.local.contactPaul Murphy, School Of Chemistry, Room 108, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedYes
dc.local.versionACCEPTED
dcterms.projectinfo:eu-repo/grantAgreement/SFI/SFI Investigator Programme/12/IA/1398/IE/Glycoside & glycoconjugate synthesis through development and application of chelation induced anomerization/en_IE
dcterms.projectinfo:eu-repo/grantAgreement/SFI/SFI Spokes Programme/14/SP/2710/IE/Gut Inflammation _ Discovery and Therapeutic Targeting of the Secretome-Receptome Inflammatory Network in Inflammatory Bowel Disease/en_IE
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Except where otherwise noted, this item's license is described as Attribution-NonCommercial-NoDerivs 3.0 Ireland