1-O-Acetyl-3,4,6-tri-O-benzyl-2-C-bromo­methyl-2-de­oxy-α-d-glucopyran­ose

Kinfe, H.H.; Makolo, F.L.; Phasha, Z.H.

doi:10.1107/S1600536812048453

Volume 69
Part 1
Page o73
January 2013

Received 16 November 2012
Accepted 26 November 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R = 0.041
wR = 0.096
Data-to-parameter ratio = 13.8
Details

1-O-Acetyl-3,4,6-tri-O-benzyl-2-C-bromomethyl-2-deoxy--D-glucopyranose

Henok H. Kinfe,^a Felix L. Makolo ^a and Zanele H. Phasha ^a ^*

^aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: zhphasha@uj.ac.za

In the title compound, C₃₀H₃₃BrO₆, the pyranose ring adopts a chair conformation. Two of the O-benzyl phenyl rings lie almost perpendicular to C/C/C/O plane formed by the ring atoms not attached to these O-benzyl phenyl rings, and form dihedral angles of 85.1 (2) and 64.6 (2)°, while the third O-benzyl phenyl ring is twisted so that it makes a dihedral angle 34.9 (2)° to this C/C/C/O plane. This twist is ascribed to the formation of an S(8) loop stabilized by a weak intramolecular C-HO hydrogen bond.

Related literature

For background to derivatization of cyclopropyl carbohydrates, see: Halton & Harvey (2006); Beyer & Madsen (1998). For details of the synthesis of the title compound, see: Gammon et al. (2007). For ring puckering analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₀H₃₃BrO₆
M_r = 569.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.5097 (4) Å
b = 19.9357 (11) Å
c = 24.4597 (16) Å
V = 2686.6 (3) Å³
Z = 4
Cu K radiation
= 2.43 mm^-1
T = 100 K
0.43 × 0.05 × 0.05 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 2008) T_min = 0.613, T_max = 0.753
51826 measured reflections
4637 independent reflections
4177 reflections with I > 2(I)
R_int = 0.097

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.096
S = 1.04
4637 reflections
335 parameters
H-atom parameters constrained
_max = 1.04 e Å^-3
_min = -0.61 e Å^-3
Absolute structure: Flack (1983), 1893 Friedel pairs
Flack parameter: -0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C18-H18O4	0.95	2.85	3.663 (7)	144

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al. 2009); software used to prepare material for publication: OLEX2.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5273 ).

Acknowledgements

Support by the research funds of the University of Johannesburg is gratefully acknowledged.

References

Beyer, J. & Madsen, R. (1998). J. Am. Chem. Soc. 120, 12137-12138.
Bruker (2008). SADABS and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gammon, D. W., Kinfe, H. H., De Vos, D. E., Jacobs, P. A. & Sels, B. F. (2007). J. Carbohydr. Chem. 26, 141-157.
Halton, B. & Harvey, J. (2006). Synlett, pp. 1975-2000.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds