188175-91-9

Upstream product

• 96073-67-5 Benzoic acid (3S,8R,9S,10R,13S,14S,17S)-17-hydroxy-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 
• 83205-52-1 3β-benzoyloxy-androst-5-en-17-one 

Downstream Products

• 188175-94-2 Benzoic acid (3S,8S,9S,10S,13S,14S,17S)-17-acetoxy-10-formyl-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 188175-93-1 Benzoic acid (3S,8R,9S,10S,13S,14S,17S)-17-acetoxy-10-hydroxymethyl-13-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 188175-92-0 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diyl 17-acetate 3-benzoate 

Relevant academic research and scientific papers

Synthesis of (19E)-3β,7β-dihydroxy-17-oxoandrost-5-EN-19-AL 19-(O-carboxymethyl)oxime, new hapten for 7β-hydroxy-dehydroepiandrosterone (3β,7β-dihydroxyandrost-5-EN-17-one)

(19E)-3β,7β-Dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime (26) was prepared in 15 steps from 17-oxoandrost-5-en-3β-yl benzoate (2, DHEA benzoate). Protection of position 17 by a borohydride reduction and acetylation, subsequent functionalization of position 19 by hypoiodite reaction, oxidation to 19-aldehyde and oximation gave successively (19E)-19-oxoandrost-5-ene-3β,17β-diyl 17-acetate 3-benzoate 19-(O-carboxymethyl)oxime methyl ester (10). Then 7-keto group was introduced hy allylic oxidation with chromium(VI) oxide-3,5-dimethylpyrazole complex and stereoselectively reduced by borohydride in the presence of cerium(III) ions into 7β-hydroxy group. After protection as 7-isobutyrate the acetate at position 17 was removed and oxidation recovered 17-ketone. Final deprotection revealed both hydroxyl and carhoxyl groups, giving desired 19 CMO 7β-hydroxy DHEA designed as hupten for immunassays.