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. 2008 May 7;64(Pt 6):o1012.
doi: 10.1107/S1600536808012567.

2-O-Benzhydryl-3,4-(S)-O-benzyl-idene-d-xylono-1,4-lactone

Sarah F Jenkinson, Sebastian D Rule, Kathrine V Booth, George W J Fleet, David J Watkin, Sigthor Petursson

2-O-Benzhydryl-3,4-(S)-O-benzyl-idene-d-xylono-1,4-lactone

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

Abstract

X-ray crystallography unequivocally shows that protection of the free hydroxyl group of 3,5-O-benzyl-idene-d-xylono-1,4-lactone with diphenyl-diazo-methane proceeded smoothly to give the title compound, C(25)H(22)O(5), with no accompanying epimerization. Unlike the analogously protected lyxono lactone, the isomeric xylono lactone has two mol-ecules present in the asymmetric unit (Z' = 2). The 5-ring lactones adopt envelope conformations and the 6-ring ketals adopt chair conformations.

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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 arbitary radius. There are two molecules in the asymmetric repeating unit.
Fig. 3.
Fig. 3.
Overlay of the two molecules in the asymmetric unit.
Fig. 4.
Fig. 4.
Packing diagram for the molecule projected along the b-axis.
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. Best, D., Jenkinson, S. F., Rule, S. D., Higham, R., Mercer, T. B., Newell, R. J., Weymouth-Wilson, A. C., Fleet, G. W. J. & Petursson, S. (2008). Tetrahedron Lett.49, 2196–2199.
    1. Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst.36, 1487.
    1. Collins, P. M. & Ferrier, R. J. (1995). In Monosaccharides: Their Chemistry and Their Roles in Natural Products. New York: John Wiley & Sons.
    1. Draths, K. M., Pompliano, D. L., Conley, D. L., Frost, J. W., Berry, A., Disbrow, G. L., Staversky, R. J. & Lievenset, J. C. (1992). J. Am. Chem. Soc.114, 3956–3962.