Formation of 1,4-anhydropyranoses from 1-O-acetyl-6-deoxy-2,3-O-isopropylidene-4-O-methylsulphonyl-α-L-manno- and talo-pyranose
Abstract
1-O-Acetyl-6-deoxy-2,3-O-isopropylidene-4-O-methylsulphonyl-α-L-mannopyranose (3) and the epimeric L-talopyranose derivative (4) yield the 1,4-anhydropyranoses (7) and (8), respectively, on treatment with sodium azide in hot NN-dimethylformamide; a possible general mechanism is suggested for these and related reactions.