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302-91-0

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Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5 α- and 5 β-series
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.
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)

Transformation of steroids by certain strains of Catenabacterium
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PREVOT,JANOT,NGUYEN-DANG-TAM
p. 3785 - 3787
(2007/10/10)

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Chemical Properties

Melting Point: 244.5 °C
Boiling Point: 545.1 °C at 760 mmHg
Flash Point:297.6 °C
Density: 1.253 g/cm³
Solubility:Ethanol (Slightly, Sonicated), Methanol (Slightly)
Storage Temp.:Refrigerator
Vapor Pressure: 3.71E-14mmHg at 25°C
Refractive Index: 1.579
PSA: 97.99000
LogP: 1.65330

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