Authentic standards for the reductive-cleavage method: the positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-l-arabinitol

Described herein is the synthesis of the eight positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-l-arabinitol. The compounds were generated simultaneously from 1,5-anhydro-l-arabinitol by sequential partial methylation and benzoylation and isolated in pure form by high-performance liquid chromatography. The desired acetates were obtained by debenzoylation and acetylation of the pure isomers. 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. Also reported for the acetates and the tri-O-methyl derivative are their linear temperature-programmed gas–liquid chromatography retention indices on three different capillary columns.