(20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether
• CAS No.: 1204023-29-9
• Molecular Formula: C₄₄H₈₂O₃Si₃
• Molecular Weight: 743.39
• Mol file: 1204023-29-9.mol

Synonyms:(20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether

Chemical Property of (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether

There total 5 articles about (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin 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: 48.0%

(20R)-des-A,B-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnan-8-one (1204023-26-6) + [2-[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide (213250-64-7) → (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether (1204023-29-9)

Guidance literature:

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

(20R)-des-A,B-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnan-8-one; In tetrahydrofuran; dibutyl ether; at -78 - 4 ℃; for 23h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.steroids.2014.01.012

Reference yield:

(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'R)-(tertbutyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnane (1204023-22-2) → (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether (1204023-29-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide / ethanol / 18 h / Reflux

2.1: dipyridinium dichromate; pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C

3.1: phenyllithium / tetrahydrofuran; dibutyl ether / 0.5 h / -20 °C / Inert atmosphere

3.2: 23 h / -78 - 4 °C / Inert atmosphere

With dipyridinium dichromate; pyridinium p-toluenesulfonate; phenyllithium; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; dibutyl ether; 3.1: |Wittig-Horner Reaction;

DOI:10.1016/j.steroids.2014.01.012

Reference yield:

(8S,20R)-de-A,B-20-[(4R)-tert-butyldimethylsilyloxy-pent-(1E)-en-yl]pregnan-8-ol (1204023-24-4) → (20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether (1204023-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dipyridinium dichromate; pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C

2.1: phenyllithium / tetrahydrofuran; dibutyl ether / 0.5 h / -20 °C / Inert atmosphere

2.2: 23 h / -78 - 4 °C / Inert atmosphere

With dipyridinium dichromate; pyridinium p-toluenesulfonate; phenyllithium; In tetrahydrofuran; dichloromethane; dibutyl ether; 2.1: |Wittig-Horner Reaction;

DOI:10.1016/j.steroids.2014.01.012

upstream raw materials:

(20R)-des-A,B-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pent-(1'E)-en-yl]-pregnan-8-one

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

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

(8S,20R)-de-A,B-20-[(4R)-tert-butyldimethylsilyloxy-pent-(1E)-en-yl]pregnan-8-ol

Downstream raw materials:

(20R,25R)-2-methylene-19,26-dinor-22-(E)-ene-1α,25-dihydroxyvitamin D3