Authentic standards for the reductive-cleavage method. The positional isomers of partially methylated and acetylated or benzoylated methyl 2-(acetylmethylamino)-2-deoxy-beta-D-glucopyranoside

Described herein is the synthesis of eight positional isomers of methylated and acetylated or benzoylated methyl 2-(acetylmethylamino)-2-deoxy-beta -D -glucopyranoside. The compounds were generated simultaneously from methyl 2 -(acetylmethylamino)-2-deoxy-beta -D-glucopyranoside by sequential partial methylation and benzoylation and isolated in pure form by high-performance liquid chromatography (HPLC). The desired acetates were obtained by debenzo ylation and acetylation of the pure isomers. Reported herein are the H-1 NM R spectra of the benzoates and the electron-ionization mass spectra of the acetates and the tri-O-methyl derivative. Also reported for the acetates an d the tri-O-methyl derivative are their linear temperature-programmed gas-l iquid chromatography (GLC) retention indices on three different capillary c olumns. (C) 2000 Elsevier Science Ltd. All rights reserved.