Synthesis, NMR and crystal characterization of dimeric terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols

Steroids. 2016 May:109:66-72. doi: 10.1016/j.steroids.2016.03.001. Epub 2016 Mar 8.

Abstract

Two dimeric steroidal terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols were prepared starting from cholesterol in a five-step synthetic sequence. X-ray crystallography shows that the obtained compounds display novel supramolecular networks in the solid state in which the facial hydrophobicity of the steroidal skeletons plays an important role. Unambiguous NMR characterization of the obtained dimers is also provided.

Keywords: Dimeric steroidal terephthalates; Epimeric 4,5-seco-cholest-3-yn-5-ols; NMR; X-ray diffraction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic
  • Cholesterol / chemistry*
  • Crystallography, X-Ray
  • Dimerization*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Phthalic Acids / chemical synthesis*
  • Phthalic Acids / chemistry*
  • Stereoisomerism

Substances

  • Phthalic Acids
  • terephthalic acid
  • Cholesterol