2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-l-xylitol (N-benzyl-l-XYLNAc)

Abstract

X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C14H20N2O3. The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal structure, intermolecular O—H...O, N—H...O and O—H...N hydrogen bonds link the molecules into chains along [100]. The carbonyl group O atom acts as an acceptor for a bifurcated hydrogen bond. The absolute configuration is determined by the use of l-glucuronolactone as the starting material for the synthesis.