Abstract
A homologous series of 1-O-acyl-D-glucopyranoses (acyl=caproyl, lauroyl, myristoyl, palmitoyl, or stearoyl) were obtained as the anomeric mixtures by condensation of the appropriate fatty acid chlorides with 2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose, followed by catalytic hydrogenation : the α anomers were predominant in all the products. Their gas-liquid chromatographic and thin-layer chromatographic behaviors were examined to establish the linear relations of log rtR or Rf values to the acyl chain-lengths. From the anomeric mixtures, their α anomer components were isolated as crystallines by repeated recrystallization. Column chromatographic separation of the acetylated anomeric mixtures furnished the pure acetates of both anomers. The infrared nuclear magnetic resonance and mass spectral features were compared between the pairs of anomers.
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