(20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether
• CAS No.: 1166898-21-0
• Molecular Formula: C₄₄H₈₄O₃Si₃
• Molecular Weight: 745.406

Synonyms:(20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether

Chemical Property of (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether

There total 8 articles about (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl 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: 89.0%

(20S)-des-A,B-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnan-8-one (1166898-19-6) + [2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (213250-64-7) → (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether (1166898-21-0)

Guidance literature:

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide; With phenyllithium; In tetrahydrofuran; 2,2'-oxybis(2-methyl-propane); at -20 ℃; for 0.5h;

(20S)-des-A,B-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnan-8-one; In tetrahydrofuran; 2,2'-oxybis(2-methyl-propane); at -78 - 0 ℃; for 21h;

Reference yield:

(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane (1166898-09-4) → (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether (1166898-21-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol

2.1: 2,6-dimethylpyridine / dichloromethane / -20 - 0 °C

3.1: ethanol; sodium hydroxide / 18 h / Reflux

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

5.1: phenyllithium / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

5.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrapropylammonium perruthennate; ethanol; palladium 10% on activated carbon; hydrogen; phenyllithium; 4-methylmorpholine N-oxide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 5.1: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm1010447

Reference yield:

(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al (115527-12-3) → (20S,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethylsilyl)oxy]-19,26-dinorvitamin D3 tert-butyldimethylsilyl ether (1166898-21-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -20 °C

1.2: 22 h / -20 - 20 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol

3.1: 2,6-dimethylpyridine / dichloromethane / -20 - 0 °C

4.1: ethanol; sodium hydroxide / 18 h / Reflux

5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / Molecular sieve

6.1: phenyllithium / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

6.2: 23 h / -78 - 4 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; tetrapropylammonium perruthennate; ethanol; palladium 10% on activated carbon; hydrogen; phenyllithium; 4-methylmorpholine N-oxide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1.1: Wittig reaction / 1.2: Wittig reaction / 6.1: Horner-Wadsworth-Emmons olefination / 6.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm1010447

upstream raw materials:

(20S)-des-A,B-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnan-8-one

[2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al

Downstream raw materials:

2-Methylene-(20S,25R)-19,26-dinor-1alpha,25-dihydroxyvitamin D₃

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