20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D₃ triisopropylsilyl ether

Base Information

• Chemical Name: 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D₃ triisopropylsilyl ether
• CAS No.: 881182-61-2
• Molecular Formula: C₄₇H₈₈O₃Si₂
• Molecular Weight: 757.385
• Mol file: 881182-61-2.mol

Synonyms:20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D₃ triisopropylsilyl ether

Chemical Property of 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D₃ triisopropylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D₃ triisopropylsilyl ether

There total 20 articles about 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D₃ triisopropylsilyl ether 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: 64.0%

20(17->12β)-abeo-25-hydroxy-des-A,B-24-trihomo-21-norcholestan-8-one (881182-34-9) + C39H63O3PSi2 → 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D3 triisopropylsilyl ether (881182-61-2)

Guidance literature:

C₃₉H₆₃O₃PSi₂; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

20(17->12β)-abeo-25-hydroxy-des-A,B-24-trihomo-21-norcholestan-8-one; In tetrahydrofuran; at -78 - -40 ℃; for 7h;

DOI:10.1021/jm049016g

Reference yield:

des-A,B-androst-9(11)-en-8β-ol (881182-38-3) → 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D3 triisopropylsilyl ether (881182-61-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 99 percent / imidazole / dimethylformamide / 20 °C

2.1: 93 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 5 h / 0 - 20 °C

3.1: 97 percent / LiNEt₂; HMPA / diethyl ether / 13 h / 20 °C

4.1: 98 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 2 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

6.1: 1.30 g / sodium naphthalenide / tetrahydrofuran / 0.33 h / -10 °C

7.1: 94 percent / H₂ / Pd/C / ethyl acetate / 2 h / 20 °C

8.1: 91 percent / pyridinium dichromate / CH₂Cl₂ / 36 h / 20 °C

9.1: lithium diisopropylamide / tetrahydrofuran; hexane / 4 h / 20 °C

9.2: 72 percent / tetrahydrofuran; hexane / 48 h / 20 °C

10.1: 99 percent / CuI; (Ph₃P)2PdCl₂ / diethylamine / 2 h / 0 - 20 °C

11.1: 92 percent / H₂ / Pd/C / ethyl acetate / 16 h / 20 °C

12.1: 97 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 48 h / Heating

13.1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

14.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C

14.2: 64 percent / tetrahydrofuran / 7 h / -78 - -40 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; dipyridinium dichromate; n-butyllithium; lithium diethylamide; tetrabutyl ammonium fluoride; hydrogen; sodium naphthalenide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; diethylamine; N,N-dimethyl-formamide;

DOI:10.1021/jm049016g

Reference yield:

2-methyl-8-nonyn-2-ol (881182-48-5) → 20(17->12β)-abeo-1α-triisopropylsilyloxy-25-hydroxy-24-trihomo-21-norvitamin D3 triisopropylsilyl ether (881182-61-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / CuI; (Ph₃P)2PdCl₂ / diethylamine / 2 h / 0 - 20 °C

2.1: 92 percent / H₂ / Pd/C / ethyl acetate / 16 h / 20 °C

3.1: 97 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 48 h / Heating

4.1: 95 percent / pyridinium dichromate / CH₂Cl₂ / 5 h / 20 °C

5.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C

5.2: 64 percent / tetrahydrofuran / 7 h / -78 - -40 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; dipyridinium dichromate; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; diethylamine;

DOI:10.1021/jm049016g

upstream raw materials:

20(17->12β)-abeo-25-hydroxy-des-A,B-24-trihomo-21-norcholestan-8-one

des-A,B-androst-9⁽¹¹⁾-en-8-one

2-methyl-8-nonyn-2-ol

des-A,B-androst-9(11)-en-8β-ol