dc.contributor.author | Wilkinson, Brendan L | |
dc.contributor.author | Bornaghi, Laurent F | |
dc.contributor.author | Poulsen, Sally-Ann | |
dc.contributor.author | Houston, Todd A | |
dc.contributor.editor | L. Ghosez | |
dc.date.accessioned | 2017-05-03T11:45:25Z | |
dc.date.available | 2017-05-03T11:45:25Z | |
dc.date.issued | 2006 | |
dc.date.modified | 2009-12-02T05:55:15Z | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.doi | 10.1016/j.tet.2006.06.001 | |
dc.identifier.uri | http://hdl.handle.net/10072/11310 | |
dc.description.abstract | We 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.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.format.extent | 358327 bytes | |
dc.format.mimetype | application/pdf | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | Elsevier | |
dc.publisher.place | United Kingdom | |
dc.publisher.uri | http://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description | |
dc.relation.ispartofstudentpublication | N | |
dc.relation.ispartofpagefrom | 8115 | |
dc.relation.ispartofpageto | 8125 | |
dc.relation.ispartofedition | 2006 | |
dc.relation.ispartofissue | 34 | |
dc.relation.ispartofjournal | Tetrahedron | |
dc.relation.ispartofvolume | 62 | |
dc.rights.retention | N | |
dc.subject.fieldofresearch | Medicinal and biomolecular chemistry | |
dc.subject.fieldofresearch | Organic chemistry | |
dc.subject.fieldofresearch | Biochemistry and cell biology | |
dc.subject.fieldofresearchcode | 3404 | |
dc.subject.fieldofresearchcode | 3405 | |
dc.subject.fieldofresearchcode | 3101 | |
dc.title | Synthetic utility of glycosyl triazoles in carbohydrate chemistry | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.faculty | Griffith 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.issued | 2006 | |
gro.hasfulltext | Full Text | |
gro.griffith.author | Poulsen, Sally-Ann | |
gro.griffith.author | Houston, Todd A. | |