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Volume 64 
Part 6 
Page o1012  
June 2008  

Received 24 April 2008
Accepted 29 April 2008
Online 7 May 2008

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Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.101
Data-to-parameter ratio = 9.1
Details
Open access

2-O-Benzhydryl-3,4-(S)-O-benzylidene-D-xylono-1,4-lactone

Sarah F. Jenkinson,a* Sebastian D. Rule,a Kathrine V. Booth,a George W. J. Fleet,a David J. Watkinb and Sigthor Peturssonc

aDepartment of Organic Chemistry, Chemical Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England,bDepartment of Chemical Crystallography, Chemical Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, and cFaculty of Business and Science, University of Akureyri, IS-600 Akureyri, Iceland
Correspondence e-mail: sarah.jenkinson@chem.ox.ac.uk

X-ray crystallography unequivocally shows that protection of the free hydroxyl group of 3,5-O-benzylidene-D-xylono-1,4-lactone with diphenyldiazomethane proceeded smoothly to give the title compound, C25H22O5, with no accompanying epimerization. Unlike the analogously protected lyxono lactone, the isomeric xylono lactone has two molecules present in the asymmetric unit (Z' = 2). The 5-ring lactones adopt envelope conformations and the 6-ring ketals adopt chair conformations.

Related literature

For related literature, see: Collins & Ferrier (1995[Collins, P. M. & Ferrier, R. J. (1995). In Monosaccharides: Their Chemistry and Their Roles in Natural Products. New York: John Wiley & Sons.]); Draths et al. (1992[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.]); Jackson et al. (1982[Jackson, G., Jones, H. F., Petursson, S. & Webber, J. M. (1982). Carbohydr. Res. 102, 147-157.]); Petursson & Webber (1982[Petursson, S. & Webber, J. M. (1982). Carbohydr. Res. 103, 41-52.]); Petursson et al. (2007[Petursson, S., Jenkinson, S. F., Booth, K. V., Weymouth-Wilson, A. C., Watkin, D. J., Fleet, G. W. J. & Best, D. (2007). Acta Cryst. E63, o4121.]); Petursson (2001[Petursson, S. (2001). Carbohydr. Res. 331, 239-245.], 2003[Petursson, S. (2003). Carbohydr. Res. 338, 963-968.]); Best et al. (2008[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.]); Jenkinson et al. (2008[Jenkinson, S. F., Rule, S. D., Booth, K. V., Fleet, G. W. J., Watkin, D. J. & Petursson, S. (2008). Acta Cryst. E64, o26.]); Görbitz (1999[Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.]).

[Scheme 1]

Experimental

Crystal data

  • C25H22O5

  • Mr = 402.45

  • Monoclinic, P 21

  • a = 14.8159 (3) Å

  • b = 9.1959 (2) Å

  • c = 15.0797 (2) Å

  • [beta] = 93.7245 (12)°

  • V = 2050.20 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.80 × 0.30 × 0.10 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.55, Tmax = 0.99

  • 25081 measured reflections

  • 4938 independent reflections

  • 3950 reflections with I > 2[sigma](I)

  • Rint = 0.047
Refinement

  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.101

  • S = 0.89

  • 4938 reflections

  • 542 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, UK.]); software used to prepare material for publication: CRYSTALS.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2623 ).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
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.  [CrossRef] [ChemPort]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [CrossRef] [details]
Collins, P. M. & Ferrier, R. J. (1995). In Monosaccharides: Their Chemistry and Their Roles in Natural Products. New York: John Wiley & Sons.
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.  [CrossRef] [ChemPort]
Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.  [ISI] [CrossRef] [details]
Jackson, G., Jones, H. F., Petursson, S. & Webber, J. M. (1982). Carbohydr. Res. 102, 147-157.  [CrossRef] [ChemPort]
Jenkinson, S. F., Rule, S. D., Booth, K. V., Fleet, G. W. J., Watkin, D. J. & Petursson, S. (2008). Acta Cryst. E64, o26.  [CrossRef] [details]
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Petursson, S. (2001). Carbohydr. Res. 331, 239-245.  [CrossRef] [PubMed] [ChemPort]
Petursson, S. (2003). Carbohydr. Res. 338, 963-968.  [CrossRef] [PubMed] [ChemPort]
Petursson, S., Jenkinson, S. F., Booth, K. V., Weymouth-Wilson, A. C., Watkin, D. J., Fleet, G. W. J. & Best, D. (2007). Acta Cryst. E63, o4121.  [CrossRef] [details]
Petursson, S. & Webber, J. M. (1982). Carbohydr. Res. 103, 41-52.  [CrossRef] [ChemPort]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, UK.

Acta Cryst (2008). E64, o1012  [ doi:10.1107/S1600536808012567 ]

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