Facile preparation of 1,6-anhydrohexoses using solvent effects and a catalytic amount of a Lewis acid.
Refluxing solutions of monosaccharides, unprotected at the 6-position and carrying O-methyl, S-ethyl, O-acetyl and OH-groups at the anomeric center, in acetonitrile containing a catalytic amount of a Lewis acid (O.1-0.4 equiv.) yielded 1,6-anhydrohexopyranoses in good to high yields. Best results were obtained with methyl 2,3,4-tri-O-dideuteriobenzyl-alpha-D-glycosides (87-91%). Dideuteriobenzyl protective groups were used to facilitate NMR spectral interpretations.
Aberg
P M
PM
Ciba-Geigy Ltd, Central Research Laboratories, Postfach, Basel, Switzerland.
Ernst
B
B
D000143:Acids; D000812:Anhydrides / Q000138:chemical synthesis; D002240:Carbohydrate Sequence; D006601:Hexoses / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D012997:Solvents
D000143:Acids; D000812:Anhydrides; D006601:Hexoses; D012997:Solvents