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 sixte en positional isomers of methylated and acetylated or benzoylated 1,5- anhydro-D-mannitol. The compounds are generated simultaneously by part ial methylation of 1,5-anhydro-D-mannitol and subsequent benzoylation, and the individual isomers are obtained in pure form by high-performa nce liquid chromatography. Debenzoylation of the latter and acetylatio n yielded the desired acetates. The H-1 NMR spectra of the benzoates a nd 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 column s.