Synthesis and characterization of authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,4-anhydro-l-fucitol

Described herein is the synthesis of all positional isomers of methylated and acetylated or benzoylated 1,4-anhydro-l-fucitol. The benzoates are generated simultaneously from 1,4-anhydro-l-fucitol 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. The 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative are reported herein as are the linear temperature programmed gas-liquid chromatography retention indices of the acetates and the tri-O-methyl derivative on three different capillary columns.