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

摘要

Addition of hydrazoic acid to alpha,beta-unsaturated aldehydes derived fromtri-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.