C-3 glucosiduronates of metabolites of adrenal steroids.
On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-D-glucuronate and silver carbonate, tetrahydrocortisone 21-acetate gave the corresponding 3-glucosiduronate triacetyl methyl ester. This product was converted into the 20-semicarbazone which, by treatment with alkali to hydrolyze the ester functions and acid to hydrolyze the semicarbazone moiety, gave tetrahydrocortisone 3-glucosiduronic acid. The acid was converted into the crystalline barium salt and into the methyl ester. An analogous series of reactions was carried out on tetrahydrocortexolone 21-acetate. Treatment of the 20-semicarbazone of tetrahydrocortisone 3-glucosiduronic acid with potassium borohydride reduced the 11-oxo function to an 11 beta hydroxyl group; acid-catalyzed removal of the semicarbazone group produced tetrahydrocortisol 3-glucosiduronic acid which also was obtained as the barium salt and the methyl ester.
D000305:Adrenal Cortex Hormones / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005965:Glucuronates / Q000138:chemical synthesis*; D013760:Tetrahydrocortisol / Q000031:analogs & derivatives / Q000138:chemical synthesis; D013761:Tetrahydrocortisone / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000305:Adrenal Cortex Hormones; D005965:Glucuronates; D013761:Tetrahydrocortisone; D013760:Tetrahydrocortisol