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. 2023 Jan:523:108739.
doi: 10.1016/j.carres.2023.108739. Epub 2023 Jan 9.

Stereoselective synthesis of glycosyl azides from anomeric hydroxides via protecting group manipulations

Sourav Nayak  1 , Somnath Yadav  2
Affiliations

Stereoselective synthesis of glycosyl azides from anomeric hydroxides via protecting group manipulations

Sourav Nayak et al. Carbohydr Res. 2023 Jan.

Abstract

Herein, we report the direct conversion of anomeric hydroxides to glycosyl azides in one step using diphenylphosphoryl azide. Protecting group manipulations on the hexose sugars have enabled the stereoselective synthesis of either the α-glycosyl azides or the β-anomeric azides in moderate to very good yields. The reaction has also been successfully used to enable the synthesis of β-2-deoxy-2-aminoglucosyl azides.

Keywords: Anomeric selectivity; Diphenylphosphoryl azide; Glycosyl azide; Protecting group manipulation.

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Conflict of interest statement

Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

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