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

M. Marsan (1) , I. Muller (1) , A. Milon (1) , W. Warnock (2) , Y. Nakatani (2) , G. Ourisson (2) , Joël Jaud (3)

1 LPTF - Laboratoire de Pharmacologie et de Toxicologie Fondamentales
2 Institut de Chimie de Strasbourg
3 CEMES - Centre d'élaboration de matériaux et d'études structurales

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,Dc=1.239 g cm−3.

Mots clés: deuterium labeled; plant sterols; Chiral sulfoxide; stigmasterol crystalline structure

Domaines: Hématologie

M. Marsan, I. Muller, A. Milon, W. Warnock, Y. Nakatani, et al.. X-ray structure determination of a chiral synthon, essential for the synthesis of 25-2H-stigmasterol. Journal of Chemical Crystallography, 1995, 25 (11), pp.783-786. ⟨10.1007/BF01670336⟩. ⟨inserm-02475423⟩