(8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]

Base Information

• Chemical Name: (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]
• CAS No.: 174505-02-3
• Molecular Formula: C₃₀H₃₈O₅
• Molecular Weight: 478.629

Synonyms:(8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]

Chemical Property of (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]

There total 3 articles about (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane] which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

4-methoxyphenylboronic acid (5720-07-0) + (8'S,9’S,10'R,13’R,14'S)-10’,13’-dimethyl-11’-(((4,4,4,4,4,4,4,4,4-nonafluoro-4112-buta-1,3-diyn-1-yl)thio)trioxidanyl)-1‘,4’,7’,8’,9’,10’, 13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[a]phenanthrene-17',2”-[1,3]dioxolane] (174505-01-2) → (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane] (174505-02-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride; In ethanol; toluene; for 42h; Inert atmosphere; Reflux;

Reference yield:

(8'S,9’S,10'R,13’S,14'S)-10’,13’-dimethyl-1',2',4',7',8',9',10’,12’,13’,14',15’,16’-dodecahydro-11’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolan]-11‘-one (13872-18-9) → (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane] (174505-02-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, RT, overnight

2: 59 percent / LiCl, 2M aq. Na₂CO₃, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / toluene; ethanol / 48 h / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium chloride; lithium diisopropyl amide; In ethanol; toluene;

DOI:10.1016/0040-4020(95)00983-3

Reference yield:

adrenosterone (382-45-6) → (8’S,9’S,10'R,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyl-1‘,4’,7’,8’,9’,10’,13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane] (174505-02-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trimethyl orthoformate; toluene-4-sulfonic acid / dichloromethane / 18 h / 40 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 20 °C / Cooling

3.1: lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol / 42 h / Inert atmosphere; Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; toluene-4-sulfonic acid; lithium chloride; lithium diisopropyl amide; trimethyl orthoformate; In tetrahydrofuran; ethanol; dichloromethane; toluene;

upstream raw materials:

4-methoxyphenylboronic acid

(8'S,9’S,10'R,13’R,14'S)-10’,13’-dimethyl-11’-(((4,4,4,4,4,4,4,4,4-nonafluoro-4112-buta-1,3-diyn-1-yl)thio)trioxidanyl)-1‘,4’,7’,8’,9’,10’, 13’,14',15’,16’-decahydro-2’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[a]phenanthrene-17',2”-[1,3]dioxolane]

(8'S,9’S,10'R,13’S,14'S)-10’,13’-dimethyl-1',2',4',7',8',9',10’,12’,13’,14',15’,16’-dodecahydro-11’H-dispiro[[1,3]dioxolane-2,3’-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolan]-11‘-one

adrenosterone

Downstream raw materials:

5-hydroxy-11β-(4-methoxyphenyl)-11α,12α-epoxy-5α-androstane-3,17-dione cyclic bis(1,2-ethanediyl acetal)

5-hydroxy-11α-(4-methoxyphenyl)-11β,12β-epoxy-5α-androstane-3,17-dione cyclic bis(1,2-ethanediyl acetal)

(5’R,8’S,9’R,10'R,11'S,12'S,13‘R,14’S)-11‘-(4-methoxyphenyl)-10’,13‘-dimethyldodecahydro-2’H-dispiro[[1,3]dioxolane-2,3‘-cyclopenta[a]phenanthrene-17’,2”-[1,3]dioxolane]-5’,12’(4’H)-diol

O-((8S,9R,10R,11S,12S,13R,14S)-11-(4-methoxyphenyl)-10,13-dimethyl-3,17-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-12-yl)-1H-imidazole-1-carbothioate

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