3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one

Base Information

• Chemical Name: 3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one
• CAS No.: 64647-72-9
• Molecular Formula: C₂₅H₄₂O₂Si
• Molecular Weight: 402.693

Synonyms:3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one

Chemical Property of 3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one

Chemical Property:

Purity/Quality:

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Technology Process of 3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one

There total 1 articles about 3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one 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:

Epietiocholanolone (571-31-3) → 3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one (64647-72-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 70 °C / Inert atmosphere

2: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3: palladium diacetate / dichloromethane; acetonitrile / 25 h / 20 °C / Inert atmosphere

With 1H-imidazole; palladium diacetate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.0c03251

Reference yield:

3β-t-butyldimethylsilyloxy-5β-androst-15-ene-17one (64647-72-9) → bufalin (465-20-3,465-21-4,33766-62-0,107033-69-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: silica gel; N-ethyl-N,N-diisopropylamine / 4 h / 80 °C / Inert atmosphere

2.1: oxygen; phenylsilane; cobalt(II) aceylacetonate / 1,4-dioxane / 5 h / 20 °C / 760.05 Torr

3.1: triethylamine; hydrazine hydrate / ethanol / 13 h / 50 °C / Inert atmosphere

3.2: 0.67 h / 0 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; lithium chloride / dimethyl sulfoxide; tetrahydrofuran / 13 h / 60 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid; sodium carbonate / dichloromethane / 5 h / -78 - -20 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

7.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

8.1: 1H-imidazole; carbon tetrabromide; triphenylphosphine / dichloromethane / 50 h / 40 °C / Inert atmosphere

9.1: oxygen; tri-n-butyl-tin hydride; triethyl borane / dichloromethane; hexane / 4 h / 20 °C / 760.05 Torr

9.2: 20 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; carbon tetrabromide; phenylsilane; oxygen; tri-n-butyl-tin hydride; silica gel; sodium carbonate; cobalt(II) aceylacetonate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; copper(l) chloride; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/acs.orglett.0c03251

upstream raw materials:

Epietiocholanolone

Downstream raw materials:

bufalin

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