5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane

Base Information

• Chemical Name: 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane
• CAS No.: 386210-55-5
• Molecular Formula: C₆₁H₆₈Cl₄O₁₂
• Molecular Weight: 1135.02
• Mol file: 386210-55-5.mol

Synonyms:5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane

Chemical Property of 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane

There total 5 articles about 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane 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: 55.6%

3,3'-dichloro-4,4'-dimethoxy-5,5'-bis(methoxycarbonyl)benzophenone (154023-65-1) + 5α-3β,17β-bis(formylmethyl)androstane (386210-54-4) → 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane (386210-55-5)

Guidance literature:

With tetrachlorobis(tetrahydrofuran)titanium(IV); zinc; In tetrahydrofuran; for 2.5h; Heating;

DOI:10.1016/S0968-0896(01)00152-3

Reference yield:

5α-3,17-bis(cyanomethylidene)androstane → 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane (386210-55-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 65 percent / sodium hydroxide / ethane-1,2-diol; H₂O / 72 h / Heating

2: 65.6 percent / potassium carbonate / acetone / 24 h / Heating

3: 98 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 48 h / 20 °C / atmospheric pressure

4: 53.7 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

5: 55.6 percent / TiCl₄*2THF complex; zinc / tetrahydrofuran / 2.5 h / Heating

With sodium hydroxide; tetrachlorobis(tetrahydrofuran)titanium(IV); hydrogen; diisobutylaluminium hydride; potassium carbonate; zinc; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethylene glycol; ethyl acetate; acetone; toluene; 5: McMurry coupling;

DOI:10.1016/S0968-0896(01)00152-3

Reference yield:

5α-3,17-bis(methoxycarbonylmethylidene)androstane (386210-52-2) → 5α-3β,17β-bis[3',3'-bis(3''-methoxycarbonyl-5''-chloro-4''-methoxyphenyl)-2'-propenyl]androstane (386210-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 48 h / 20 °C / atmospheric pressure

2: 53.7 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

3: 55.6 percent / TiCl₄*2THF complex; zinc / tetrahydrofuran / 2.5 h / Heating

With tetrachlorobis(tetrahydrofuran)titanium(IV); hydrogen; diisobutylaluminium hydride; zinc; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 3: McMurry coupling;

DOI:10.1016/S0968-0896(01)00152-3

upstream raw materials:

3,3'-dichloro-4,4'-dimethoxy-5,5'-bis(methoxycarbonyl)benzophenone

5α-3β,17β-bis(formylmethyl)androstane

5α-3,17-bis(methoxycarbonylmethylidene)androstane

5α-3,17-bis(carboxymethylidene)androstane