The preparation of estradiol-17 beta sulfates with triethylamine-sulfur trioxide.
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.
D055598:Chemical Phenomena; D002621:Chemistry; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005021:Ethylamines; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013461:Sulfur Oxides
D005021:Ethylamines; D007202:Indicators and Reagents; D013461:Sulfur Oxides; C048615:estradiol 17-sulfate; D004958:Estradiol; C011118:sulfur trioxide; C016162:triethylamine