187219-48-3

Upstream product

• 108-24-7 acetic anhydride 
• 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 

Downstream Products

• 187219-53-0 Benzoic acid (3S,8R,9S,10R,13S,14S,17S)-17-acetoxy-15-[(E)-methoxycarbonylmethoxyimino]-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 
• 187219-56-3 Benzoic acid (3S,8R,9S,10R,13S,14S)-15-[(E)-methoxycarbonylmethoxyimino]-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 187219-54-1 Benzoic acid (3S,8R,9S,10R,13S,14S,17S)-17-hydroxy-15-[(E)-methoxycarbonylmethoxyimino]-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

Synthesis of (15E)-3β-hydroxyandrost-5-ene-15,17-dione 15-(O-carboxymethyl)oxime; The new hapten for 3β-hydroxyandrost-5-en-17-one(dehydroepiandrosterone, dhea)

From 17β-hydroxy-15β-[(4-methoxyphenyl)methoxy]androst-5-en-3β-yl acetate (1) by acetylation, removal of (4-methoxyphenyl)methyl group, and oxidation with Jones reagent, 15-oxoandrost-5-ene-3β,17β-diyl 3,17-diacetate (4) was prepared. (O-Carboxymethyl)hydroxylamine treatment and subsequent diazomethane methylation gave methyl ester of corresponding 15-(O-carboxymethyl)oxime derivative. Partial acid hydrolysis gave 3-acetate as a minor product, therefore the major 17-acetate was transformed in two steps into the 3-benzoate. Oxidation at position 17 and subsequent deprotection gave for both products final (15E)-3β-hydroxyandrost-5-ene-15,17-dione 15-(O-carboxymethyl)oxime (14), but for 3-acetyl derivative the whole synthesis is shorter and gave higher yield.