Three N-chlorophenyl-2-deoxy-α-D-pyranosylamine compounds (1, 2 and 3) were synthesized through a reaction of 2-deoxy-D-ribose with different chlorobenzenamines in water and methanol. Their structures were identified by means of 1H NMR and 13C NMR spectra. Pure N-chlorophenyl-2-deoxy- α-D-ribopyranosylamine was dissolved in d6-DMSO with an additional drop of heavy water at room temperature. It was found that compound 1 isomerized to four configurational isomers, which was confirmed by 1H NMR and 13C NMR analyses. Single crystals of compounds 1, 2 and 3 were grown and their crystal structures were determined by a single crystal diffraction technique. The reason why the reaction gives only a pyranose configuration compound was explained. And the isomerization mechanism of compound 1 was explored.

Key words: N-chlorophenyl-2-deoxy-α-D-ribopyranosylamine, stereoselective synthesis, configuration, isomer