174815-53-3

Upstream product

• 17921-63-0 3β-hydroxy-androst-5,15-dien-17-one 
• 108-24-7 acetic anhydride 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 174815-58-8 Acetic acid (3S,8R,9S,10R,13S,14S,15R,17S)-17-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-15-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 174815-59-9 (3S,8R,9S,10R,13S,14S,15R,17S)-17-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-15-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 174815-60-2 (8R,9S,10R,13S,14S,15R,17S)-17-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-15-(4-methoxy-benzyloxy)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 174815-67-9 (3S,8R,9S,10R,13S,14S,15R,17S)-17-(Isopropyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 174815-68-0 (8R,9S,10R,13S,14S,15R,17S)-17-(Isopropyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one 
• 2226-70-2 15beta-Hydroxytestosterone 
• 174815-57-7 Acetic acid (3S,8R,9S,10R,13S,14S,15R,17S)-17-hydroxy-15-(4-methoxy-benzyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 

Relevant academic research and scientific papers

Chemical synthesis of 15β-hydroxytestosterone and its derivatives using a (4-methoxyphenyl)methyl protecting group

Reaction of 3β-hydroxyandrosta-5,15-dien-17-one with 4-methoxybenzyl alcohol followed by acetylation gave mainly 15β-[(4-methoxyphenyl)methoxy]- 17-oxoandrost-5-en-3β-yl acetate. This product was transformed by borohydrate reduction and organosilyl derivatization into the orthogonally protected 17β-(dimethylthexylsiloxy)-15β-[(4-methoxyphenyl)methoxy]androst- 5-en-3β-yl acetate and 17β-(dimethylisopropylsiloxy)-15β-[4- methoxyphenyl]methoxylandrost-5-en-3β-yl acetate and 17β- (dimethylisopropylsiloxy)-15β-[4-methoxyphenyl)methoxy]androst-5-en-3β-yl acetate. After deacetylation, these intermediates were submitted to Oppenauer oxidation and both yielded testosterone derivatives 17β- (dimethylthexylsiloxy)-15β-[(4-methoxyphenyl)methoxy]androst-4-en-one and 17β-(dimethylisopropylsiloxy)-15β-[(4-methoxyphenyl)-methoxy]androst-4-en- 3-one. Removal of the (4-methoxyphenyl)methyl group from position 15 by 2.3- dichloro-5,6-dicyano-1,4-benzoquinone treatment gave the partially protected derivatives 17β-(dimethylthexylsiloxy)-15β-hydroxyandrost-4-en-3-one and 17β-(dimethylisopropylsiloxy)-15β-hydroxyandrost-4-en-3-one. After acidic deprotection, the dimethylthexylsilyl derivative yielded 15β- hydroxystestosterone (15β,17β-dihydroxyandrost-4-en-3-one). Dimethylisopropylsilyl derivative was converted to the corresponding 15- hemisuccinate and 15-hemiglutarate (17β-hydroxy-3-oxoandrost-4-en-15β-yl 15-hemisuccinate and 15-hemiglutarate, respectively), which were designed as model haptens for immunoassays studies.