(3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene

Base Information

• Chemical Name: (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene
• CAS No.: 1061330-15-1
• Molecular Formula: C₂₇H₄₃BrO₃Si
• Molecular Weight: 523.626
• Mol file: 1061330-15-1.mol

Synonyms:(3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene

Chemical Property of (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene

There total 10 articles about (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene 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: 72.0%

hexylidenetriphenylphosphoran (16666-79-8,19493-12-0) + 2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde (1061330-14-0) → (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene (1061330-15-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/ol8014804

Reference yield:

(R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enone (1061330-08-2) → (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene (1061330-15-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bromine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 21 °C / Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

4.2: 1 h / -78 °C / Inert atmosphere

With bromine; sodium hexamethyldisilazane; titanium tetrachloride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm400959q

Reference yield:

(R)-2-bromo-4-(4-methoxyphenylmethoxy)cyclopent-2-enone (1061330-09-3) → (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene (1061330-15-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: titanium tetrachloride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

With sodium hexamethyldisilazane; titanium tetrachloride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm400959q

upstream raw materials:

hexylidenetriphenylphosphoran

2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde

(R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enone

(R)-2-bromo-4-(4-methoxyphenylmethoxy)cyclopent-2-enone

Downstream raw materials:

(αRS)-α-((4R,5R)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-methoxyphenylmethoxy)-5-((Z)-oct-2-enyl)cyclopent-1-enyl)-(2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]-butyl)oxirane-2-methanol

4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanal

4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid