Chemical and Biochemical Studies on Carbohydrate Esters. I. Preparation and Properties of 1-O-Acyl-β-D-glucopyranose Tetraacetates

Abstract

A series of 1-O-acyl-β-D-glucopyranose tetraacetates were prepared by reaction of α-acetobromoglucose with the silver salts of the eleven, normal, saturated fatty acids, i.e., propanoic, butanoic, pentanoic, hexanoic, octanoic, nonanoic, decanoic, dodecanoic, tetradecanoic, hexadecanoic, and octadecanoic acids. Exclusive production of β-anomers was confirmed by measurement of their specific rotations and also by observing their IR and NMR spectra. The characteristic mass spectral features were discussed for these analogs. Gas liquid chromatography was found to be recommendable for the qualitative and quantitative analyses of this type of compounds.