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dc.contributor.authorWilkinson, Brendanen_US
dc.contributor.authorBornaghi, Laurenten_US
dc.contributor.authorPoulsen, Sally-Annen_US
dc.contributor.authorHouston, Todden_US
dc.contributor.editorL. Ghosezen_US
dc.date.accessioned2017-04-24T08:40:33Z
dc.date.available2017-04-24T08:40:33Z
dc.date.issued2006en_US
dc.date.modified2009-12-02T05:55:15Z
dc.identifier.issn0040-4020en_US
dc.identifier.doi10.1016/j.tet.2006.06.001en_AU
dc.identifier.urihttp://hdl.handle.net/10072/11310
dc.description.abstractWe report herein a study of the synthetic utility of the glucosyl triazole moiety in carbohydrate chemistry. A model glucosyl triazole was prepared by a modified Huisgen 1,3-dipolar cycloaddition reaction. The relative rate of cycloaddition was investigated using a variety of alcohol co-solvents and reaction temperatures. It was found that the reaction proceeded with similar efficiency irrespective of co-solvent, however mildly elevated temperatures (40 àcf. rt) increased the speed of reaction significantly (2 h cf. 8 h). The robustness of the triazole moiety was then interrogated under conditions typically encountered in carbohydrate chemistry reaction sequences-alcohol group protection/deprotection, nucleophilic displacement, and O-glycosylation. The triazole integrity was retained in all cases studied as evidenced from full compound characterization. Finally, a diverse set of triazole-linked glycoconjugates was synthesized. Collectively, our results demonstrated that the glucosyl triazole moiety was indeed a robust entity for carbohydrate chemistry.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.format.extent358327 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherElsevieren_US
dc.publisher.placeUnited Kingdomen_US
dc.publisher.urihttp://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#descriptionen_AU
dc.relation.ispartofstudentpublicationNen_AU
dc.relation.ispartofpagefrom8115en_US
dc.relation.ispartofpageto8125en_US
dc.relation.ispartofedition2006en_US
dc.relation.ispartofissue34en_US
dc.relation.ispartofjournalTetrahedronen_US
dc.relation.ispartofvolume62en_US
dc.rights.retentionNen_AU
dc.subject.fieldofresearchcode250301en_US
dc.titleSynthetic utility of glycosyl triazoles in carbohydrate chemistryen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.facultyGriffith Sciences, School of Natural Sciencesen_US
gro.rights.copyrightCopyright 2006 Elsevier. Reproduced in accordance with the copyright policy of the publisher. This journal is available online - use hypertext links.en_AU
gro.date.issued2006
gro.hasfulltextFull Text


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