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X-ray structure determination of a chiral synthon, essential for the synthesis of 25-2H-stigmasterol

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Abstract

Synthesis of sterols with varying side chains, including deuterium labeled stigmasterol and sitosterol may be performed via the Wittig-Horner coupling of a 22 aldehyde derived from stigmasterol and a suitable sulfoxide derivative of the side chain. The X-ray structure determination of this synthon have been performed since it is a crucial step in order to know the absolute configuration of the chiral carbon atoms. Crystallographic data were as follows:a=7.437(2),b=10.103(4),c=10.274(3)Å, β=100.32(6)o, =759.4 Å3, space group P21 (No.4),Z=2,D c=1.239 g cm−3.

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Authors and Affiliations

  1. Laboratoire de Pharmacologie et de Toxicologie Fondamentales, CNRS, 118 rte de Narbonne, 31062, Toulouse, France

    M. P. Marsan, I. Muller & A. Milon

  2. Laboratoire de Chimie Organique des Substances Naturelles, associé au CNRS, Centre de Neurochimie, 5 rue Blaise Pascal, 67084, Strasbourg, France

    W. Warnock, Y. Nakatani & G. Ourisson

  3. Centre Elaboration de Matériaux et d'Etudes Structurales, CNRS, BP 4347, 31055, Toulouse Cedex, France

    J. Jaud

Authors
  1. M. P. Marsan
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  2. I. Muller
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  3. A. Milon
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  4. W. Warnock
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  5. Y. Nakatani
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  6. G. Ourisson
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  7. J. Jaud
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Marsan, M.P., Muller, I., Milon, A. et al. X-ray structure determination of a chiral synthon, essential for the synthesis of 25-2H-stigmasterol. J Chem Crystallogr 25, 783–786 (1995). https://doi.org/10.1007/BF01670336

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  • DOI: https://doi.org/10.1007/BF01670336

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