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Hydrogen fluoride-catalyzed formation of glycosides. Preparation of methyl 2-acetamido-2-deoxy-β-d-gluco- and -β-d-galacto-pyranosides, and of β-(1→6)-linked 2-acetamido-2-deoxy-d-gluco- and -d-galacto-pyranosyl oligosaccharides

✍ Scribed by Jacques Defaye; Andrée Gadelle; Christian Pedersen

Publisher
Elsevier Science
Year
1989
Tongue
English
Weight
775 KB
Volume
186
Category
Article
ISSN
0008-6215

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✦ Synopsis

Dissolution of 2-acetamido-2-deoxy-D-glucose

(1) or -D-galactose (2) in anhydrous hydrogen fluoride, followed by addition of methanol, gave stereospecifitally the corresponding methyl J?-D-glycopyranosides 7 and 8. When solutions of 1 or 2 in hydrogen fluoride were slowly evaporated, mixtures of exclusively ED-(1+6)-linked di-to hexa-sacch~des containing 2-acetamido-2-deoxy-glu~osy~ (9) and -galactosyl (10) residues were obtained; these were separated by gel permeation chromatography to give pure products. Compounds 7 and 9 were also obtained when solutions of chitin were treated under appropriate conditions. *Dedicated to Prof. Edgar Lederer on the occasion of his 80th birthday.

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