Baeyer-Villiger reaction of steroid sapogenins by CF3COOH-H2O2. A short cut to pregnan-3β,16β,20-triol 3-monoacetates

Steroids. 2017 Dec:128:1-5. doi: 10.1016/j.steroids.2017.10.001. Epub 2017 Oct 10.

Abstract

Treatment of steroid sapogenins with H2O2 in CF3COOH for 15min followed by reflux in CH3OH/H2O afforded good yields of pregnan-3β,16β,20-triol 3-monoacetates. When the hydrolysis step was carried out with KOH in refluxing methanol excellent yields pregnantriols were obtained. The resulting compounds were characterized by their melting points and NMR spectral data. An X-ray diffraction analysis of compound 3a confirmed the proposed structure and provided detailed information about the bond lengths, bond angles and conformation.

Keywords: Baeyer-Villiger reaction; NMR; Pregnan-3β,16β,20-triol monoacetates; Pregnan-3β,16β,20-triols; Steroid sapogenins; X-ray diffraction analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Peroxide / chemistry
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Pregnanolone / chemistry*
  • Sapogenins / chemical synthesis
  • Sapogenins / chemistry*
  • Stereoisomerism
  • Steroids / chemical synthesis
  • Steroids / chemistry*
  • Transition Temperature

Substances

  • Sapogenins
  • Steroids
  • Hydrogen Peroxide
  • Pregnanolone