Determination of the absolute configuration of monosaccharides using (+) or (-) 2-tert-butyl-2-methyl-1,3-benzodioxole-4- carboxylic acid and high-resolution 1H-n.m.r. spectroscopy

Article abstract of DOI:10.1016/0008-6215(91)84086-T

Reaction of (-) 2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid with per-O-acetyl-D- and L-glucopyranosyl bromides yielded diastereomeric per-O-acetylated glycopyranosyl 2-tert-butyl-2-methyl-1,3-benzodiazole-4-carboxylates. Their ¹H-n.m.r. signals, especially the strong singlet peaks of tert-Bu and Me groups in the 1-ester portion were diagnostic for the determination of the D,L-configuration and optical purity of monosaccharides. Reaction of (-)2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylic acid with per-O-acetyl-D-and L-glucopyranosyl bromides yielded diastereomeric per-O-acetylated glycopyranosyl 2-tert-butyl-2-methyl-1, 3-benzodiazole-4-carboxylates. Their H-n.m.r. signals, especially the strong singlet peaks of tert-bu and Me groups in the 1-ester portion were diagnostic for the determination of the D,L-configuration and optical purity of monosaccharides.