3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane

Base Information

• Chemical Name: 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane
• CAS No.: 226713-94-6
• Molecular Formula: C₃₀H₄₄OSi
• Molecular Weight: 448.764
• Mol file: 226713-94-6.mol

Synonyms:3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane

Chemical Property of 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane

There total 6 articles about 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-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: 80.0%

phenyldimethylsilyl chloride (768-33-2) + 17-(Z)-ethylidene-3β-hydroxy-6-methylene-5α-androstane (226714-49-4) → 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane (226713-94-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 2.5h;

DOI:10.1021/ja9808595

Reference yield:

17β-hydroxy-5α-androstane-3,6-dione (899-39-8) → 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane (226713-94-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 42.4 percent / p-TsOH / 0.08 h / Heating

2: 93 percent / potassium tert-butoxide / tetrahydrofuran / Ambient temperature

3: CrO₃, H₂SO₄ / acetone / 1 h / 20 °C

4: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / -78 °C

5: 75 percent / potassium tert-butoxide / tetrahydrofuran / 4.5 h / Ambient temperature

6: 80 percent / triethylamine / dimethylformamide / 2.5 h

With chromium(VI) oxide; lithium tri(t-butoxy)aluminum hydride; sulfuric acid; potassium tert-butylate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja9808595

Reference yield:

6-methylene-5α-androstane-3,17-dione (4729-50-4) → 3β-((dimethylphenylsilyl)oxy)-17-(Z)-ethylidene-6-methylene-5α-androstane (226713-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / -78 °C

2: 75 percent / potassium tert-butoxide / tetrahydrofuran / 4.5 h / Ambient temperature

3: 80 percent / triethylamine / dimethylformamide / 2.5 h

With lithium tri(t-butoxy)aluminum hydride; potassium tert-butylate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja9808595

upstream raw materials:

phenyldimethylsilyl chloride

17-(Z)-ethylidene-3β-hydroxy-6-methylene-5α-androstane

17β-hydroxy-5α-androstane-3,6-dione

6-methylene-5α-androstane-3,17-dione

Refernces