Methyl 5-O-(4-chloro­benzo­yl)-2-de­oxy-3-O-methyl­sulfonyl-threo-pentofuran­oside

Jiang, H.; Li, H.; Sun, H.

doi:10.1107/S1600536810007087

Volume 66
Part 4
Page o820
April 2010

Received 26 January 2010
Accepted 24 February 2010
Online 13 March 2010

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.006 Å
R = 0.061
wR = 0.160
Data-to-parameter ratio = 17.7
Details

Methyl 5-O-(4-chlorobenzoyl)-2-deoxy-3-O-methylsulfonyl-threo-pentofuranoside

Hongshi Jiang,^a ^* Hui Li ^a and Hong Sun ^a

^aDepartment of Applied Chemistry, Yuncheng University, Yuncheng, Shanxi 044000, People's Republic of China
Correspondence e-mail: jianghongshi555@126.com

In the chiral title compound, C₁₄H₁₇ClO₇S, an intermediate in the synthesis of the AIDS treatment drug zidovudine, the threose ring adopts an envelope configuration, with the O atom at the flap position.

Related literature

For general background to the title compound, see: Li & Yan (2009).

Experimental

Crystal data

C₁₄H₁₇ClO₇S
M_r = 364.79
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.3103 (11) Å
b = 10.996 (2) Å
c = 28.559 (6) Å
V = 1667.6 (6) Å³
Z = 4
Mo K radiation
= 0.39 mm^-1
T = 113 K
0.16 × 0.04 × 0.02 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.941, T_max = 0.992
10486 measured reflections
3708 independent reflections
2350 reflections with I > 2(I)
R_int = 0.081

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.160
S = 0.96
3708 reflections
210 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.35 e Å^-3
Absolute structure: Flack (1983), 1491 Friedel pairs
Flack parameter: 0.14 (12)

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5317 ).

Acknowledgements

We thank the College Research Program of Yuncheng University (2008112) for funding.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Li, J. L. & Yan, L. (2009). Chin. Patent No. 101376667
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds