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Volume 69 
Part 12 
Page o1811  
December 2013  

Received 10 November 2013
Accepted 13 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.009 Å
Disorder in main residue
R = 0.056
wR = 0.255
Data-to-parameter ratio = 8.2
Details
Open access

(-)-Benzyl 2,3-dide­oxy-[beta]-D-erythro-hex-2-eno­pyran­oside

aResearch and Education Center for Natural Sciences, Keio University, Hiyoshi 4-1-1, Kohoku-ku, Yokohama 223-8521, Japan, and bDepartment of Pharmaceutical Science, Keio University, Shibakoen 1-5-30, Minato-ku, Tokyo 105-8512, Japan
Correspondence e-mail: ohba@a3.keio.jp

In the title compound, C13H16O4, the six-membered ring of the sugar moiety shows a half-chair conformation. In the crystal, mol­ecules are connected via O-H...O hydrogen bonds, forming columns around twofold screw axes along the b-axis direction. There is a disorder of the benz­yloxy group, which has two possible orientations with the phenyl group lying on a common plane [site-occupancy factors = 0.589 (9) and 0.411 (9)].

Related literature

For the phenolic Ferrier reaction, see: Ferrier & Prasad (1969[Ferrier, R. J. & Prasad, N. (1969). J. Chem. Soc. C, pp. 570-575.]); Noshita et al. (1995[Noshita, T., Sugiyama, T., Kitazumi, Y. & Oritani, T. (1995). Biosci. Biotechnol. Biochem. 59, 2052-2055.]). For the structure of the related compound [alpha]-glycoside, see: Wingert et al. (1984[Wingert, L. M., Ruble, J. R. & Jeffrey, G. A. (1984). Carbohydr. Res. 128, 1-10.]). For the synthesis of [beta]-glycoside, see: Di Bussolo et al. (2002[Di Bussolo, V., Caselli, M., Pineschi, M. & Crotti, P. (2002). Org. Lett. 4, 3695-3698.], 2004[Di Bussolo, V., Caselli, M., Romano, M. R., Pineschi, M. & Crotti, P. (2004). J. Org. Chem. 69, 8702-8708.]). For the enzymatic regioselective acyl­ation of D-glucal, see: Calveras et al. (2010[Calveras, J., Nagai, Y., Sultana, I., Ueda, Y., Higashi, T., Shoji, M. & Sugai, T. (2010). Tetrahedron, 66, 4284-4291.]).

[Scheme 1]

Experimental

Crystal data
  • C13H16O4

  • Mr = 236.26

  • Monoclinic, P 21

  • a = 19.500 (9) Å

  • b = 5.291 (2) Å

  • c = 6.0809 (15) Å

  • [beta] = 94.27 (3)°

  • V = 625.7 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 292 K

  • 0.60 × 0.40 × 0.20 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 1713 measured reflections

  • 1585 independent reflections

  • 786 reflections with F2 > 2[sigma](F2)

  • Rint = 0.034

  • 3 standard reflections every 150 reflections intensity decay: 0.8%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.255

  • S = 1.04

  • 1579 reflections

  • 193 parameters

  • 33 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O3i 0.82 1.95 2.692 (8) 151
O3-H3...O2ii 0.82 1.89 2.614 (8) 147
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+2]; (ii) x, y+1, z.

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC Diffractometer Control Software (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); data reduction: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5321 ).


Acknowledgements

This work was supported by the Keio Gijuku Academic Development Funds.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Calveras, J., Nagai, Y., Sultana, I., Ueda, Y., Higashi, T., Shoji, M. & Sugai, T. (2010). Tetrahedron, 66, 4284-4291.  [Web of Science] [CrossRef] [ChemPort]
Di Bussolo, V., Caselli, M., Pineschi, M. & Crotti, P. (2002). Org. Lett. 4, 3695-3698.  [PubMed] [ChemPort]
Di Bussolo, V., Caselli, M., Romano, M. R., Pineschi, M. & Crotti, P. (2004). J. Org. Chem. 69, 8702-8708.  [CrossRef] [PubMed] [ChemPort]
Ferrier, R. J. & Prasad, N. (1969). J. Chem. Soc. C, pp. 570-575.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Noshita, T., Sugiyama, T., Kitazumi, Y. & Oritani, T. (1995). Biosci. Biotechnol. Biochem. 59, 2052-2055.  [CrossRef] [ChemPort]
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wingert, L. M., Ruble, J. R. & Jeffrey, G. A. (1984). Carbohydr. Res. 128, 1-10.  [CSD] [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1811  [ doi:10.1107/S1600536813031140 ]

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