312-99-2Relevant articles and documents
Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5 α- and 5 β-series
Okihara, Rika,Mitamura, Kuniko,Hasegawa, Maki,Mori, Megumi,Muto, Akina,Kakiyama, Genta,Ogawa, Shoujiro,Iida, Takashi,Shimada, Miki,Mano, Nariyasu,Ikegawa, Shigeo
experimental part, p. 344 - 353 (2011/02/22)
Here, we describe the chemical synthesis of the complete sets of 18 novel 3- and 21-monosulfates and their double-conjugated form of tetrahydrocortisol (THF), tetrahydro-11-deoxycortisol (THS), and tetrahydrocortisone (THE) in the 5 α- and 5 β-series. The principal reactions involved are: (1) selective protection of a specific hydroxy group in substrates; (2) catalytic hydrogenation at C-5 of Δ4-3-ketosteroids with 10% Pd(OH) 2/C to yield 3-oxo-5 β-steroids and reductive allomerization with 10% Pd/C to yield 3-oxo-5 α-isomers; (3) reduction of the resulting 3-oxo-5 β- and 3-oxo-5 α-steroids to the corresponding 3 α-hydroxy-compounds with Zn(BH4)2 and K-Selectride, respectively; and (4) sulfation of hydroxy groups at C-3 and/or C-21 in the tetrahydrocorticosteroid derivatives with sulfur trioxide-triethylamine complex.
Ruthenium-Catalyzed Oxidative Transformation of Alkenes to α-Ketols with Peracetic Acid. Simple Synthesis of Cortisone Acetate
Murahashi, Shun-Ichi,Saito, Takao,Hanaoka, Hidenori,Murakami, Yoshihide,Naota, Takeshi,et al.
, p. 2929 - 2930 (2007/10/02)
The reactions of alkenes with peracetic acid in the presence of RuCl3 catalyst gave the corresponding α-ketols, which are important building units for synthesis of biological active compounds, such as cortisone acetate.
Chemical conversion of corticosteroids to 3α,5α-tetrahydro derivatives. Synthesis of allotetrahydro-11-deoxycortisol glucuronides
Hosoda,Takasaki,Miura,et al.
, p. 4281 - 4287 (2007/10/02)
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