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Volume 70 
Part 5 
Pages o561-o562  
May 2014  

Received 3 March 2014
Accepted 9 April 2014
Online 16 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.081
Data-to-parameter ratio = 9.4
Details
Open access

Methyl 4-O-benzyl-[alpha]-L-rhamno­pyrano­side

aDepartment of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden, and bDepartment of Materials and Environmental Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden
Correspondence e-mail: lars.eriksson@mmk.su.se

In the title compound, C14H20O5, an inter­mediate in the synthesis of oligosaccharides, the glycosidic [H-C-O-C(H3)] torsion angle [varphi]H is 52.3° and the exo-cyclic [H-C-O-C(H2)] torsion angle [theta]H is -11.7°. The hexa­pyran­ose ring has a chair conformation. In the crystal, mol­ecules are linked by O-H...O hydrogen bonds, forming chains propagating along [010]. Enclosed within the chains are R33(12) ring motifs involving three mol­ecules. The chains are linked via C-H...[pi] inter­actions, forming a three-dimensional network.

Related literature

For a description of L-rhamnose as part of polysaccharides, see: Ansaruzzaman et al. (1996[Ansaruzzaman, M., Albert, M. J., Holme, T., Jansson, P.-E., Rahman, M. M. & Widmalm, G. (1996). Eur. J. Biochem. 237, 786-791.]); Marie et al. (1998[Marie, C., Weintraub, A. & Widmalm, G. (1998). Eur. J. Biochem. 254, 378-381.]); Säwén et al. (2012[Säwén, E., Östervall, J., Landersjö, C., Edblad, M., Weintraub, A., Ansaruzzaman, M. & Widmalm, G. (2012). Carbohydr. Res. 348, 99-103.]). For a description of syntheses in which the title compound has been used, see: Eklund et al. (2005[Eklund, R., Lycknert, K., Söderman, P. & Widmalm, G. (2005). J. Phys. Chem. B, 109, 19936-19945.]); Handa et al. (1979[Handa, V. K., Piskorz, C. F., Barlow, J. J. & Matta, K. L. (1979). Carbohydr. Res. 74, C5-C7.]). For the structure of rhamnosyl-containing tris­accharides, see: Eriksson & Widmalm (2012[Eriksson, L. & Widmalm, G. (2012). Acta Cryst. E68, o2221-o2222.]); Eriksson et al. (1999[Eriksson, L., Söderman, P. & Widmalm, G. (1999). Acta Cryst. C55, 1736-1738.]); Jonsson et al. (2006[Jonsson, K. H. M., Eriksson, L. & Widmalm, G. (2006). Acta Cryst. C62, o447-o449.]). For further related literature on L-rhamnose, see: Anderson & Ijeh (1994[Anderson, J. E. & Ijeh, A. I. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 1965-1967.]); Varki et al. (1999[Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G. & Marth, J. (1999). Editors. Essentials of Glycobiology. Cold Spring Harbor: Cold Spring Harbor Laboratory Press.]); Haines (1969[Haines, A. H. (1969). Carbohydr. Res. 10, 466-467.]); Herget et al. (2008[Herget, S., Toukach, P. V., Ranzinger, R., Hull, W. E., Knirel, Y. A. & von der Lieth, C.-W. (2008). BMC Struct. Biol. 8, article No. 35 (pp. 1-20).]); Olsson et al. (2005[Olsson, U., Lycknert, K., Stenutz, R., Weintraub, A. & Widmalm, G. (2005). Carbohydr. Res. 340, 167-171.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H20O5

  • Mr = 268.30

  • Orthorhombic, P 21 21 21

  • a = 6.5377 (1) Å

  • b = 9.1848 (2) Å

  • c = 23.2699 (5) Å

  • V = 1397.30 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.25 × 0.12 × 0.05 mm

Data collection
  • Oxford Diffraction Xcalibur 3 with sapphire 3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2004[Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.921, Tmax = 1.000

  • 9540 measured reflections

  • 1665 independent reflections

  • 1407 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.081

  • S = 1.00

  • 1665 reflections

  • 177 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C41-C46 benzyl ring.

D-H...A D-H H...A D...A D-H...A
O2-H2A...O3i 0.82 2.00 2.813 (2) 172
O3-H3A...O5ii 0.82 2.05 2.799 (2) 151
C7-H7C...Cgiii 0.96 2.89 3.652 (3) 137
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (ii) x-1, y, z; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2004[Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2004[Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2001[Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Germany.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: SU2708 ).


Acknowledgements

This work was supported by grants from the Swedish Research Council and the Knut and Alice Wallenberg foundation.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Anderson, J. E. & Ijeh, A. I. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 1965-1967.  [CrossRef]
Ansaruzzaman, M., Albert, M. J., Holme, T., Jansson, P.-E., Rahman, M. M. & Widmalm, G. (1996). Eur. J. Biochem. 237, 786-791.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Eklund, R., Lycknert, K., Söderman, P. & Widmalm, G. (2005). J. Phys. Chem. B, 109, 19936-19945.  [CrossRef] [PubMed] [ChemPort]
Eriksson, L., Söderman, P. & Widmalm, G. (1999). Acta Cryst. C55, 1736-1738.  [CSD] [CrossRef] [IUCr Journals]
Eriksson, L. & Widmalm, G. (2012). Acta Cryst. E68, o2221-o2222.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Haines, A. H. (1969). Carbohydr. Res. 10, 466-467.  [CrossRef] [ChemPort] [Web of Science]
Handa, V. K., Piskorz, C. F., Barlow, J. J. & Matta, K. L. (1979). Carbohydr. Res. 74, C5-C7.  [CrossRef] [Web of Science]
Herget, S., Toukach, P. V., Ranzinger, R., Hull, W. E., Knirel, Y. A. & von der Lieth, C.-W. (2008). BMC Struct. Biol. 8, article No. 35 (pp. 1-20).  [CrossRef]
Jonsson, K. H. M., Eriksson, L. & Widmalm, G. (2006). Acta Cryst. C62, o447-o449.  [CSD] [CrossRef] [IUCr Journals]
Marie, C., Weintraub, A. & Widmalm, G. (1998). Eur. J. Biochem. 254, 378-381.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Olsson, U., Lycknert, K., Stenutz, R., Weintraub, A. & Widmalm, G. (2005). Carbohydr. Res. 340, 167-171.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2004). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Säwén, E., Östervall, J., Landersjö, C., Edblad, M., Weintraub, A., Ansaruzzaman, M. & Widmalm, G. (2012). Carbohydr. Res. 348, 99-103.  [Web of Science] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G. & Marth, J. (1999). Editors. Essentials of Glycobiology. Cold Spring Harbor: Cold Spring Harbor Laboratory Press.


Acta Cryst (2014). E70, o561-o562   [ doi:10.1107/S1600536814007922 ]

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