Potential Corticoid Metabolites: Chemical Synthesis of 3-and 21-Monosulfates and Their Double-Conjugates of Tetrahydrocorticosteroids in the 5. ALPHA.-and 5. …

R Okihara, K Mitamura, M Hasegawa, M Mori…

Index: Okihara, Rika; Mitamura, Kuniko; Hasegawa, Maki; Mori, Megumi; Muto, Akina; Kakiyama, Genta; Ogawa, Shoujiro; Iida, Takashi; Shimada, Miki; Mano, Nariyasu; Ikegawa, Shigeo Chemical and Pharmaceutical Bulletin, 2010 , vol. 58, # 3 p. 344 - 353

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Citation Number: 7

Abstract

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 5α-and 5β-series. The principal reactions involved are:(1) selective protection of a specific hydroxy group in substrates;(2) catalytic hydrogenation at C-5 of Δ 4-3-ketosteroids with 10% Pd (OH) 2/C to yield 3-oxo- ...

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