AuBr 3 -catalyzed azidation of per- O -acetylated and per- O -benzoylated sugars

AuBr 3 -catalyzed azidation of per- O -acetylated and per- O -benzoylated sugars

Herein we report, for the first time, the successful anomeric azidation of per- -acetylated and per- -benzoylated sugars by catalytic amounts of oxophilic AuBr in good to excellent yields. The method is applicable to a wide range of easily accessible per- -acetylated and per- -benzoylated sugars. Wh...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry Vol. 14; pp. 682 - 687
Main Authors: Rajput, Jayashree, Hotha, Srinivas, Vangala, Madhuri
Format: Journal Article
Language:English
Published: Germany 22-03-2018
Subjects:
N-glycoside
acylated sugars
azidation
gold(III) bromide
oxophilicity
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Summary:Herein we report, for the first time, the successful anomeric azidation of per- -acetylated and per- -benzoylated sugars by catalytic amounts of oxophilic AuBr in good to excellent yields. The method is applicable to a wide range of easily accessible per- -acetylated and per- -benzoylated sugars. While reaction with per- -acetylated and per- -benzoylated monosaccharides was complete within 1-3 h at room temperature, the per- -benzoylated disaccharides needed 2-3 h of heating at 55 °C.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.14.56