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

Article abstract of DOI:10.1016/0008-6215(89)84033-9

Dissolution of 2-acetamido-2-deoxy-D-glucose (1) or -D-galactose (2) in anhydrous hydrogen fluoride, followed by addition of methanol, gave stereospecifically the corresponding methyl β-D-glycopyranosides 7 and 8.When solutions of 1 or 2 in hydrogen fluoride were slowly evaporated, mixtures of exclusively β-D-(1->6)-linked di- to hexa-saccharides containing 2-acetamido-2-deoxy-glucosyl (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.