(8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene

Base Information

• Chemical Name: (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene
• CAS No.: 213337-06-5
• Molecular Formula: C₂₇H₃₀O
• Molecular Weight: 370.535
• Mol file: 213337-06-5.mol

Synonyms:(8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene

Chemical Property of (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene

There total 4 articles about (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene 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: 79.0%

tri-n-butyl(vinyl)tin (7486-35-3) + (8R,9S,13S,14S)-3-(benzyloxy)-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate (213337-05-4) → (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene (213337-06-5)

Guidance literature:

With lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 2h; Heating;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1965::AID-EJOC1965>3.0.CO;2-S

Reference yield:

Estrone (53-16-7) → (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene (213337-06-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / K₂CO₃ / CH₂Cl₂; methanol / Heating

2: 95 percent / LiN3)3>2 / tetrahydrofuran / 2 h / -78 - 25 °C

3: 79 percent / LiCl, / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

With potassium carbonate; lithium chloride; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1965::AID-EJOC1965>3.0.CO;2-S

Reference yield:

3-benzyloxyestra-1,3,5(10)-trien-17-one (858-98-0) → (8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene (213337-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiN3)3>2 / tetrahydrofuran / 2 h / -78 - 25 °C

2: 79 percent / LiCl, / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

With lithium chloride; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1002/(SICI)1099-0690(199809)1998:9<1965::AID-EJOC1965>3.0.CO;2-S

upstream raw materials:

tri-n-butyl(vinyl)tin

(8R,9S,13S,14S)-3-(benzyloxy)-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate

Estrone

3-benzyloxyestra-1,3,5⁽¹⁰⁾-trien-17-one

Downstream raw materials:

17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5⁽¹⁰⁾,16-tetraene

C₂₉H₃₄O

C₂₉H₃₄O

C₂₉H₃₄O