5α-androst-16-en-3β-yl acetate

Base Information

• Chemical Name: 5α-androst-16-en-3β-yl acetate
• CAS No.: 72203-76-0
• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.484
• Mol file: 72203-76-0.mol

Synonyms:5α-androst-16-en-3β-yl acetate

Chemical Property of 5α-androst-16-en-3β-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5α-androst-16-en-3β-yl acetate

There total 6 articles about 5α-androst-16-en-3β-yl acetate 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:

3β-acetoxy-5α-androstan-17-one (1239-31-2) → 5α-androst-16-en-3β-yl acetate (72203-76-0) + 3β-acetyloxy-17-(4’-methyphenyl)-5α-androst-16-ene (144067-35-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 - 20 °C / Inert atmosphere

2: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium tert-butylate / toluene / 2 h / 50 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / benzene; methanol; water / Schlenk technique; Reflux

With bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; potassium hexamethylsilazane; sodium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; toluene; benzene; 2: |Suzuki-Miyaura Coupling / 3: |Suzuki-Miyaura Coupling;

DOI:10.1039/C6OB02496C

Reference yield:

Epiandrosterone (481-29-8) → 5α-androst-16-en-3β-yl acetate (72203-76-0) + 3β-acetyloxy-17-(4’-methyphenyl)-5α-androst-16-ene (144067-35-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 20 °C / Inert atmosphere

2: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 - 20 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium tert-butylate / toluene / 2 h / 50 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / benzene; methanol; water / Schlenk technique; Reflux

With pyridine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; potassium hexamethylsilazane; sodium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; toluene; benzene; 3: |Suzuki-Miyaura Coupling / 4: |Suzuki-Miyaura Coupling;

DOI:10.1039/C6OB02496C

Reference yield:

para-bromotoluene (106-38-7) + 3β-acetyloxy-17-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolan-2-yl)-5α-androst-16-ene → 5α-androst-16-en-3β-yl acetate (72203-76-0) + 3β-acetyloxy-17-(4’-methyphenyl)-5α-androst-16-ene (144067-35-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In methanol; water; benzene; Overall yield = 36 mg; Schlenk technique; Reflux;

DOI:10.1039/C6OB02496C

upstream raw materials:

acetic anhydride

17β-nitroamino-5α-androstan-3β-yl acetate

3β-acetoxy-5α-androstan-17-one

para-bromotoluene

Downstream raw materials:

3β-acetoxy-4'ξ-[(tert-butyl-dimethyl-silanyloxy)-methyl]-2'-cyclohexyl-(5α,16β,17β)-tetrahydro-androstano[16,17-e][1,2]oxazine-3'ξ-carbonitrile

3β-acetoxy-2'-cyclohexyl-4'ξ-hydroxymethyl-(5α,16β,17β)-tetrahydro-androstano[16,17-e][1,2]oxazine-3'ξ-carbonitrile

5α-androst-16-en-3β-ol

3β-acetoxy-2'-cyclohexyl-4'ξ-hydroxymethyl-(5α,16β,17β)-tetrahydro-androstano[16,17-e][1,2]oxazine-3'ξ-carboxylic acid lactone