Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2010 Apr 24;66(Pt 5):o1147-8.
doi: 10.1107/S1600536810014145.

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

Sarah F Jenkinson, Elizabeth V Crabtree, Andreas F G Glawar, Terry D Butters, George W J Fleet, David J Watkin

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

Sarah F Jenkinson et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-l-XYLNAc, C(14)H(20)N(2)O(3). 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, inter-molecular O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules 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.

PubMed Disclaimer

Figures

Fig. 1.
Fig. 1.
Synthetic Scheme
Fig. 2.
Fig. 2.
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
Fig. 3.
Fig. 3.
Packing diagram of the title compound with hydrogen bonds shown by dotted lines.
See this image and copyright information in PMC

References

    1. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
    1. Asano, N., Nash, R. J., Molyneux, R. J. & Fleet, G. W. J. (2000). Tetrahedron Asymmetry, 11, 1645–1680.
    1. Best, D., Chairatana, P., Glawar, A. F. G., Crabtree, E., Butters, T. D., Wilson, F. X., Yu, C.-Y., Wang, W.-B., Jia, Y.-M., Adachi, I., Kato, A. & Fleet, G. W. J. (2010). Tetrahedron Lett.51, 2222–2224.
    1. Best, D., Wang, C., Weymouth-Wilson, A. C., Clarkson, R. A., Wilson, F. X., Nash, R. J., Miyauchi, S., Kato, A. & Fleet, G. W. J. (2010). Tetrahedron Asymmetry, 21, 311–319.
    1. Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst.36, 1487.