Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1389849 | Carbohydrate Research | 2007 | 7 Pages |
Abstract
A carbohydrate-based oxepine, derived from 2-deoxy-d-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the β-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Steve Castro, Emily C. Cherney, Nicole L. Snyder, Mark W. Peczuh,