Abstract
Conformations of four 3, 6-disubstituted derivatives of methyl α-D-altropyranoside in various solvents were studied by nuclear magnetic resonance spectroscopy. The derivatives examined included methyl 3, 6-diamino-3, 6-dideoxy-α-D-altropyranoside (I), its di-N-acetate (II), tetar-O, N-acetate (III) and methyl 3, 6-diazido-3, 6-dideoxy-α-D-altropyranoside (IV). Analysis of the spectra revealed that the predominant conformation in all the cases was C1, but I and II in deuterium oxide were shown to exist partly in the 1C conformation. IV in deuteriochloroform existed probably in a mixture of three conformers. Infrared spectroscopy indicated that the conformers of IV in inert solvents existed in the intramolecularly hydrogen bonded forms. The resonance data of methyl 6-azido-6-deoxy-2-O-methanesulfonyl-α-D-glucopyranoside (X) and methyl 2, 6-di-O-methanesulfonyl-α-D-glucopyranoside (XI) were added.
