Synthetic utility of glycosyl triazoles in carbohydrate chemistry

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Title Synthetic utility of glycosyl triazoles in carbohydrate chemistry
Author Wilkinson, Brendan Luke; Bornaghi, Laurent; Poulsen, Sally-Ann; Houston, Todd Ashley
Journal Name Tetrahedron
Editor L. Ghosez
Year Published 2006
Place of publication United Kingdom
Publisher Pergamon
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 °C cf. 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.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description
Alternative URI http://dx.doi.org/10.1016/j.tet.2006.06.001
Copyright Statement Copyright 2006 Elsevier. Reproduced in accordance with the copyright policy of the publisher. This journal is available online - use hypertext links.
Volume 62
Issue Number 34
Edition 2006
Page from 8115
Page to 8125
ISSN 0040-4020
Date Accessioned 2007-02-02
Date Available 2009-12-02T05:55:15Z
Language en_AU
Research Centre Eskitis Institute for Drug Discovery; Institute for Glycomics
Faculty Faculty of Science, Environment, Engineering and Technology
Subject PRE2009-Organic Chemical Synthesis
URI http://hdl.handle.net/10072/11310
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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