56162-40-4Relevant academic research and scientific papers
C-3 GLUCOSIDURONATES OF METABOLITES OF ADRENAL STEROIDS
Mattox, Vernon R.,Goodrich, June E.,Nelson, Albert N.
, p. 23 - 34 (2007/10/02)
On treatment with methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-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 11β 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.
