Microwave-assisted synthesis of deuterium labeled estrogen fatty acid esters

Article abstract of DOI:10.1016/j.steroids.2005.08.001

Deuterated analogs of estrogen fatty acid esters are needed as internal standards for isotope dilution GC/MS analyses. We have developed a rapid and efficient synthesis for 2,4,16,16-D₄-estrone palmitate, stearate, oleate, linoleate, and linolenate and the corresponding 2,4,16,16,17α- D₅-estradiol fatty acid 17-mono and 3,17-diesters using analogous fatty acid chlorides or fatty acid anhydrides and 4-(dimethylamino)pyridine under microwave irradiation. Chemoselective hydrolysis of fatty acid diesters was carried out by KOH in t-BuOH.