Synthesis of the anomers of methyl 2-acetamido-2-deoxy-d-galacto-furanoside and -pyranoside

On treatment with methanol in the presence of Amberlite IR-120 (H⁺) resin, 2-acetamido-2-deoxy-d-galactose yielded a mixture of four isomers, the methyl 2-acetamido-2-deoxy-α- and -β-d-galactofuranosides and their corresponding pyranosides. The isomers were separated preparatively on Dowex-1 ion-exchange resin, and analytically by high-pressure liquid chromatography, and identified by their m.p. and specific rotation and by assays of periodate uptake and formaldehyde liberated.