Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated 1,5-anhydro-d-mannitol

Described herein is an efficient method for the synthesis of the sixteen positional isomers of methylated and acetylated or benzoylated 1,5-anhydro-d-mannitol. The compounds are generated simultaneously by partial methylation of 1,5-anhydro-d-mannitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performance liquid chromatography. Debenzoylation of the latter and acetylation yielded the desired acetates. The 1H NMR spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tetra-O-methyl derivative are reported herein as are the linear temperature-programmed gas-liquid chromatography retention indices of the acetates and the tetra-O-methyl derivative on three different capillary columns.