(1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene

Base Information

• Chemical Name: (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene
• CAS No.: 115648-68-5
• Molecular Formula: C₃₉H₆₆O₃Si₂
• Molecular Weight: 639.122
• Mol file: 115648-68-5.mol

Synonyms:

Chemical Property of (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene

There total 4 articles about (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10⁽¹⁹⁾-triene 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:

Cyclopropyl methyl ketone (765-43-5) → (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene (115648-68-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature

2: 84 percent

3: 86 percent / 2N sodium hydroxide / H₂O; CH₂Cl₂

4: dimethylsulfoxide / 4 h / 105 °C

With sodium hydroxide; bromine; In methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)86903-9

Reference yield:

2-bromo-1-cyclopropylethan-1-one (69267-75-0) → (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene (115648-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent

2: 86 percent / 2N sodium hydroxide / H₂O; CH₂Cl₂

3: dimethylsulfoxide / 4 h / 105 °C

With sodium hydroxide; In dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)86903-9

Reference yield:

(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide (112849-15-7) → (1S,3R,20S)-bis(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxyprop-1'(E)-enyl)-9,10-secopregna-5(E),7(E),10(19)-triene (115648-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 2N sodium hydroxide / H₂O; CH₂Cl₂

2: dimethylsulfoxide / 4 h / 105 °C

With sodium hydroxide; In dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)86903-9

upstream raw materials:

1-cyclopropyl-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one

2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propionaldehyde

Cyclopropyl methyl ketone

2-bromo-1-cyclopropylethan-1-one