The use of tri- O-acetyl- d-glucal and - d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides

Abstract

Addition of hydrazoic acid to α,β-unsaturated aldehydes derived from tri- O-acetyl- d-glucal and - d-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri- O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the 1H and 13 C NMR, IR and polarimetric data.