55592-40-0

Upstream product

• 200722-01-6 4-[(6S,7S,8R,9S,13S,14S,17S)-6-(Imidazole-1-carbothioyloxy)-13-methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester 
• 200721-99-9 4-[(6S,7S,8R,9S,13S,14S,17S)-6-Hydroxy-13-methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester 
• 200721-98-8 4-[(7S,8R,9S,13S,14S,17S)-13-Methyl-6-oxo-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl]-butyric acid methyl ester 
• 200722-03-8 3,17β-bis(2-trimethylsilyl)ethoxymethyl-7α-(3'-carbomethoxypropyl)estradiol 
• 200721-96-6 (7S,8R,9S,13S,14S,17S)-13-Methyl-7-pent-4-enyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-6-one 
• 191674-87-0 (8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(2-trimethylsilanyl-ethoxymethoxy)-7,8,9,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-6-one 
• 68325-09-7 4-((7R,8R,9S,13S,14S,17S)-3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl)-butyric acid methyl ester 

Relevant academic research and scientific papers

A stereoselective synthesis of 7α-(3'-carboxypropyl)estradiol from a noncontrolled substance

Alkylation of 3.17β-bis(2-trimethylsilyl)ethoxymethyl-1,3,5(10) estratriene-6-one (2) with 5-bromo-1-pentene using NaHMDS in THF afforded 3,17β-bis(2-trimethylsilyl)ethoxymethyl-7-α-(4'-pentenyl)- 1,3,5(10)estratriene-6-one (3) in excellent stereoselectivity (>95% epimeric excess). Functionalization of the side chain in compound 3 was accomplished via ozonolysis, oxidation and esterification to give 5 in 72% yield. The reduction of ester (5) using NaBH4 in MeOH afforded the corresponding 6α- hydroxy compound (6) as a single isomer in 72% yield. The hydroxyl group in 6 was removed by converting to the corresponding xanthate (7) followed by reduction rising n-Bu3SnH to afford 8 in good yield. Finally, the SEM protective groups in 8 were removed, after which the ester function was hydrolyzed with LiOH to give 7α-(3'-carboxypropyl)estradiol (10), in 10.6% overall yield from 3.