Steroid conjugates IV. The preparation of steroid sulfates with triethylamine-sulfur trioxide

Chemical sulfation of small molecules—advances and challenges

“…Another example is the synthesis of 2-sulfated form of α- l -iduronate glycosides using 1.5 equivalents of SO 3 -NMe 3 per -OH group in dry DMF at 55 °C for 24 h 57. A lengthy series of steroid sulfates have been prepared using SO 3 -NEt 3 complex in which selective sulfation was observed for unhindered hydroxyl groups at room temperature, while heating to 70 – 95 °C led to sulfation of hindered alcoholic groups 58. Polyhydroxysteroids have also been sulfated using 1.5 equivalents of SO 3 -NEt 3 per hydroxyl group at 95 °C 59.…”

The steroid sulfatase inhibitor COUMATE attenuates rather than enhances access of dehydroepiandrosterone sulfate to the brain in the mouse

“…Filters were then placed in 3 ml of scintillation fluid (Ecoscint H, National Diagnostics, UK) for the measurement (Dusza et al 1968), cleaned by solvent extraction (Corsan et al 1997) and then purified by celite chromatography in the solvent system (v/v) isooctane (20); tert-butanol (40): water (39): ammonia (1). Thin layer chromatography of the final product on silica gel 60 coated plates in ethyl acetate/ethanol/ammonia (25/10/2 v/v) revealed a purity of greater than 99%.…”

Stimulation of 16α-Hydroxylation of Dehydroisoandrosterone Sulfate by Diethylstilbestrol

“…A Packard radiochromatogram scanner was used to localize the bands of radioactivity on the paper strips. Selective sulfation of the 3(3-hydroxyl group was achieved following the procedure described by Dusza et al (16). The labeled 3 H-16a-HOD eluted from paper after the second chromatography, was dissolved in 1 drop of pyridine and mixed with about 1 mg of crystalline triethylamine-sulfur trioxide reagent.…”