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

Date Published: May 01, 2010

Publisher: International Union of Crystallography

Author(s): Sarah. F. Jenkinson, Elizabeth. V. Crabtree, Andreas. F. G. Glawar, Terry D. Butters, George. W. J. Fleet, David. J. Watkin.


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.

Partial Text

For imino­sugars see: Asano et al. (2000 ▶); Watson et al. (2001 ▶). For the inhibition of hexosaminidases, see: Liu, Numa et al. (2004 ▶); Reese et al. (2007 ▶); Liu, Iqbal et al. (2004 ▶); Woynarowska et al. (1992 ▶). For piperidine hexosaminidase inhibitors, see: Tatsuta et al. (1997 ▶); Fleet et al. (1986 ▶, 1987 ▶); Steiner et al. (2009 ▶); Ho et al. (2010 ▶); For furan­ose hexosaminidase inhibitors, see: Usuki et al. (2009 ▶); Rountree et al. (2007 ▶, 2009 ▶); Boomkamp et al. (2010 ▶). For strategies for cancer treatment, see: Kato et al. (2010 ▶); Greco et al. (2009 ▶). For the use of glucuronolactone as a starting material for the synthesis of imino­sugars, see: Best, Wang et al. (2010 ▶); Best, Chairatana et al. (2010 ▶).




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