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Volume 69 
Part 5 
Page o632  
May 2013  

Received 28 January 2013
Accepted 19 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.073
Data-to-parameter ratio = 22.7
Details
Open access

(3R,4S,5R)-Methyl 3,5-bis[(tert-butyldimethylsilyl)oxy]-4-methoxycyclohex-1-enecarboxylate

aSchool of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, People's Republic of China, and bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
Correspondence e-mail: liyl@tjipr.com

The title compound, C21H42O5Si2, was synthesized from (3R,4S,5R)-methyl 3,5-bis[(tert-butyldimethylsilyl)oxy]-4-hydroxycyclohex-1-enecarboxylate by an esterification reaction. The cyclohexene ring adopts a half-chair conformation. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming helical chains propagating along [010].

Related literature

The title compound is an intermediate in the synthesis of vandetanib {systematic name: N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methyl-4-piperidinyl)methoxy]-4-quinazolinamine} derivatives. For vandetanib as a tyrosine kinase inhibitor, see: Heymach (2005[Heymach, J. V. (2005). Br. J. Cancer, 92(Suppl 1), 14-20.]); Morabito et al. (2009[Morabito, A., Piccirillo, M. C., Falasconi, F., De Feo, G., Del Giudice, A., Bryce, J., Di Maio, M., De Maio, E., Normanno, N. & Perrone, F. (2009). Oncologist, 14, 378-390.]); Wells et al. (2010[Wells, S. A., Gosnell, J. E., Gagel, R. F., Moley, J., Pfister, D., Sosa, J. A., Skinner, M., Krebs, A., Vasselli, J. & Schlumberger, M. (2010). J. Clin. Oncol. 28, 767-772.]); Natale et al. (2009[Natale, R. B., Thongprasert, S., Greco, F. A., Thomas, M., Tsai, C. M., Sunpaweravong, P., Ferry, D., Langmuir, P., Rowbottom, J. A. & Goss, G. D. (2009). J. Clin. Oncol. 27(15S), abstr. 8009.]).

[Scheme 1]

Experimental

Crystal data
  • C21H42O5Si2

  • Mr = 430.72

  • Monoclinic, P 21

  • a = 10.760 (5) Å

  • b = 8.321 (4) Å

  • c = 14.601 (7) Å

  • [beta] = 98.997 (9)°

  • V = 1291.3 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.968, Tmax = 0.981

  • 13589 measured reflections

  • 6015 independent reflections

  • 4456 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.073

  • S = 0.98

  • 6015 reflections

  • 265 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2745 Friedel pairs

  • Flack parameter: -0.04 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7B...O3i 0.98 2.55 3.410 (3) 147
C9-H9A...O3ii 0.98 2.59 3.527 (3) 161
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1].

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2187 ).


Acknowledgements

The synthesis and evaluation of the title compound was undertaken as part of the National Science and Technology Major Project "The synthesis and anticancer activity screening of novel chalcone derivatives". The authors thank the State Key Laboratory of Elemento-organic Chemistry Nankai University, for the X-ray data collection.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Heymach, J. V. (2005). Br. J. Cancer, 92(Suppl 1), 14-20.
Morabito, A., Piccirillo, M. C., Falasconi, F., De Feo, G., Del Giudice, A., Bryce, J., Di Maio, M., De Maio, E., Normanno, N. & Perrone, F. (2009). Oncologist, 14, 378-390.  [CrossRef] [PubMed] [ChemPort]
Natale, R. B., Thongprasert, S., Greco, F. A., Thomas, M., Tsai, C. M., Sunpaweravong, P., Ferry, D., Langmuir, P., Rowbottom, J. A. & Goss, G. D. (2009). J. Clin. Oncol. 27(15S), abstr. 8009.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2006). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wells, S. A., Gosnell, J. E., Gagel, R. F., Moley, J., Pfister, D., Sosa, J. A., Skinner, M., Krebs, A., Vasselli, J. & Schlumberger, M. (2010). J. Clin. Oncol. 28, 767-772.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o632  [ doi:10.1107/S1600536813007551 ]

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