20997-98-2Relevant academic research and scientific papers
A fusion method for the preparation of steroid sulfates
Dusza,Joseph,Bernstein
, p. 317 - 323 (1985)
A method for the preparation of steroid triethylammonium sulfates is outlined which involves the fusion of triethylamine-sulfur trioxide and steroids. Experimental details are presented which define the process as a thermal equilibrium resulting in the preferential sulfation of aliphatic hydroxyl groups. Salfation of an aromatic hydroxyl group can be achieved in the absence of an aliphatic hydroxyl group. With excess reagent both types of hydroxyl groups in the same molecule can be sulfated.
A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates
Waller, Christopher C.,McLeod, Malcolm D.
supporting information, p. 74 - 80 (2015/02/19)
Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17β-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17β-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17β-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 μg of testosterone (17β-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS).
