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dc.contributor.authorWilkinson, Brendan L
dc.contributor.authorBornaghi, Laurent F
dc.contributor.authorPoulsen, Sally-Ann
dc.contributor.authorHouston, Todd A
dc.contributor.editorL. Ghosez
dc.date.accessioned2017-05-03T11:45:25Z
dc.date.available2017-05-03T11:45:25Z
dc.date.issued2006
dc.date.modified2009-12-02T05:55:15Z
dc.identifier.issn0040-4020
dc.identifier.doi10.1016/j.tet.2006.06.001
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.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent358327 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherElsevier
dc.publisher.placeUnited Kingdom
dc.publisher.urihttp://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom8115
dc.relation.ispartofpageto8125
dc.relation.ispartofedition2006
dc.relation.ispartofissue34
dc.relation.ispartofjournalTetrahedron
dc.relation.ispartofvolume62
dc.rights.retentionN
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchBiochemistry and cell biology
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode3101
dc.titleSynthetic utility of glycosyl triazoles in carbohydrate chemistry
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, School of Natural Sciences
gro.rights.copyright© 2006 Elsevier. Reproduced in accordance with the copyright policy of the publisher. This journal is available online - use hypertext links.
gro.date.issued2006
gro.hasfulltextFull Text
gro.griffith.authorPoulsen, Sally-Ann
gro.griffith.authorHouston, Todd A.


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