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. 2018 Mar 22:14:682-687.
doi: 10.3762/bjoc.14.56. eCollection 2018.

AuBr3-catalyzed azidation of per- O-acetylated and per- O-benzoylated sugars

Jayashree Rajput  1 , Srinivas Hotha  1 , Madhuri Vangala  1
Affiliations

AuBr3-catalyzed azidation of per- O-acetylated and per- O-benzoylated sugars

Jayashree Rajput et al. Beilstein J Org Chem. .

Abstract

Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr3 in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1-3 h at room temperature, the per-O-benzoylated disaccharides needed 2-3 h of heating at 55 °C.

Keywords: N-glycoside; acylated sugars; azidation; gold(III) bromide; oxophilicity.

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Figures

Scheme 1
Scheme 1
Azidation of per O-acetylated glucose.
See this image and copyright information in PMC

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