17736-20-8Relevant articles and documents
C-3 GLUCOSIDURONATES OF METABOLITES OF ADRENAL STEROIDS
Mattox, Vernon R.,Goodrich, June E.,Nelson, Albert N.
, p. 23 - 34 (1982)
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.
A novel synthesis of tetrahydrocortisone 3-glucuronide
Aisa, Haji A.,Jiang, Xiangrui,Li, Rui,Shen, Jingshan,Zhang, Suqing,Zhang, Yan
, (2022/01/19)
A new route for the synthesis of tetrahydrocortisone 3-glucuronide has been developed with cortisone acetate as a starting material. The key step was using lithium tri-tert-butoxyaluminum hydride to reduce the C-3 carbonyl group of 5β-dihydrocortisone acetate (8) to provide 3α-5β-tetrahydrocortisone acetate (5). Then, Koenig–Knorr method was used for glycosylation with glycosyl bromide as the donor, cadmium carbonate as promoter and 4? molecular sieves as dehydrating agent to give high yield of the desired product. The new route is shorter and gives higher yield than that reported in the literature.
