Synthesis and characterization of authentic standards for the analysis of ribofuranose-containing carbohydrates by the reductive-cleavage method

Described herein is the synthesis of all positional isomers of partially methylated and acetylated or benzoylated 1,4-anhydro-d-ribitol. The benzoates are generated simultaneously from 1,4-anhydro-d-ribitol by sequential partial methylation and benzoylation or sequential partial benzoylation and methylation. The individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation and acetylation provided the corresponding acetates. Reported herein are the 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative and also for the acetates and the tri-O-methyl derivative, their linear temperature programmed gas-liquid chromatography retention indices on three different capillary columns.