The preparation of estradiol-17 beta sulfates with triethylamine-sulfur trioxide

Steroids. 1985 Mar-Apr;45(3-4):303-15. doi: 10.1016/0039-128x(85)90079-0.

Abstract

Reaction of estradiol-17 beta with triethylamine-sulfur trioxide in pyridine gives exclusively monosulfation at the C17-hydroxyl group with the preparation of 17 beta-sulfooxyestra-1,3,5(10)-trien-3-ol triethylammonium salt (V). The structural assignment suggested by spectroscopic measurements was confirmed by synthetic studies. (Formula: see text) A synthesis of 3-sulfooxyestra-1,3,5(10)-trien-17 beta-ol triethylammonium salt (II) has been accomplished based on the preparation of 17 beta-formyloxyestra-1,3,5(10)-trien-3-ol (XIII). Fusion of the 3-sulfate triethylammonium salt II gives rise to the 17-sulfate triethylamine salt V. The preparation of estradiol-17 beta disulfate has also been achieved.

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Estradiol / analogs & derivatives*
  • Estradiol / chemical synthesis
  • Ethylamines
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Optical Rotation
  • Spectrophotometry, Infrared
  • Sulfur Oxides

Substances

  • Ethylamines
  • Indicators and Reagents
  • Sulfur Oxides
  • estradiol 17-sulfate
  • Estradiol
  • sulfur trioxide
  • triethylamine