One-pot azidochlorination of glycals.
A simple one-pot azidochlorination for the preparation of nitrogen-containing Koenigs-Knorr glycosyl donors proceeds upon reaction of protected glycals with sodium azide, ferric chloride, and hydrogen peroxide. Different mono- and disaccharide galactals and glucals are converted in a highly α-selective manner to the 2-azido glycosyl chlorides. Starting from disaccharide galactals, building blocks for the synthesis of the T-antigen are obtained in a straightforward manner. The simplicity of the reaction conditions allows for an efficient and scalable α-selective synthesis of 2-azido substituted glycosyl chlorides.
Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstr. 25, 33615 Bielefeld, Germany.
Carolin
C
Plattner
Michael
M
Höfener
Norbert
N
Sewald
D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D015394:Molecular Structure
D001386:Azides; D002241:Carbohydrates; D006027:Glycosides