Synthetic utility of glycosyl triazoles in carbohydrate chemistry

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Wilkinson, Brendan L
Bornaghi, Laurent F
Poulsen, Sally-Ann
Houston, Todd A
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L. Ghosez

Date
2006
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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.

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Tetrahedron

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62

Issue

34

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© 2006 Elsevier. Reproduced in accordance with the copyright policy of the publisher. This journal is available online - use hypertext links.

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Medicinal and biomolecular chemistry

Organic chemistry

Biochemistry and cell biology

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