(14β)-5α-Androstane

Base Information

• Chemical Name: (14β)-5α-Androstane
• CAS No.: 22511-92-8
• Molecular Weight: 260.45738
• Mol file: 22511-92-8.mol

Synonyms:

Chemical Property of (14β)-5α-Androstane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (14β)-5α-Androstane

There total 22 articles about (14β)-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: 81.0%

13β,14β-methano-18-nor-5α-androstane → 5α,14β-androstane (438-22-2,438-23-3,1757-51-3,3986-82-1,4030-91-5,10085-13-9,13077-81-1,15885-55-9,22511-92-8,24887-75-0,35457-05-7,28805-72-3)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1002/chem.201502148

Reference yield:

17β-(hydroxymethyl)-5α-androstane → 5α,14β-androstane (438-22-2,438-23-3,1757-51-3,3986-82-1,4030-91-5,10085-13-9,13077-81-1,15885-55-9,22511-92-8,24887-75-0,35457-05-7,28805-72-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: tert.-butylnitrite / chloroform / 0.5 h / Darkness

1.2: 0.33 h / 20 °C / Irradiation; Inert atmosphere

2.1: 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 0.17 h

2.2: 24 h / 40 °C

3.1: tributylphosphine / tetrahydrofuran / 3 h / 66 °C

4.1: dihydrogen peroxide / tetrahydrofuran; water / 4 h / 66 °C

5.1: potassium dioxotetrahydroxoosmate(VI); 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone; tert-butyl alcohol / 40 h / 23 °C

6.1: sodium periodate / tetrahydrofuran; water / 4 h / Reflux

7.1: toluene-4-sulfonic acid / water; benzene / 16 h / Reflux; Dean-Stark

8.1: W₂-Raney nickel / ethanol / 3.5 h / 100 °C

9.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 h / 66 °C

10.1: sodium nitrite / dichloromethane; acetic acid / 2 h / 23 °C

11.1: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / -20 °C

With triethylsilane; sodium periodate; lithium aluminium tetrahydride; tert.-butylnitrite; potassium dioxotetrahydroxoosmate(VI); tributylphosphine; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; sodium nitrite; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; acetic acid; acetone; tert-butyl alcohol; benzene; 1.1: |Barton Nitrite Photolysis / 1.2: |Barton Nitrite Photolysis;

DOI:10.1002/chem.201502148

Reference yield:

17-oxo-5α-androstano-18-nitrile → 5α,14β-androstane (438-22-2,438-23-3,1757-51-3,3986-82-1,4030-91-5,10085-13-9,13077-81-1,15885-55-9,22511-92-8,24887-75-0,35457-05-7,28805-72-3)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / water; benzene / 16 h / Reflux; Dean-Stark

2: W₂-Raney nickel / ethanol / 3.5 h / 100 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 20 h / 66 °C

4: sodium nitrite / dichloromethane; acetic acid / 2 h / 23 °C

5: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / -20 °C

With triethylsilane; lithium aluminium tetrahydride; toluene-4-sulfonic acid; trifluoroacetic acid; sodium nitrite; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; benzene;

DOI:10.1002/chem.201502148

Refernces

• 1、 Fetizon,Gramain. "Synthesis in the 5-alpha, 13-alpha androstane series". . p. 1003 - 1009. Retrieved 2007/10/05.