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

Base Information

• Chemical Name: 2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde
• CAS No.: 1061330-14-0
• Molecular Formula: C₂₁H₃₁BrO₄Si
• Molecular Weight: 455.464
• Mol file: 1061330-14-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about 2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde 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: 66.0%

2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]ethanol (1061330-11-7) → 2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde (1061330-14-0)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 22 ℃; for 1h;

DOI:10.1021/ol8014804

Reference yield:

(R)-2-bromo-4-(4-methoxyphenylmethoxy)cyclopent-2-enone (1061330-09-3) → 2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde (1061330-14-0)

Guidance literature:

Multi-step reaction with 2 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

With titanium tetrachloride; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jm400959q

Reference yield:

(R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enone (1061330-08-2) → 2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde (1061330-14-0)

Guidance literature:

Multi-step reaction with 3 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

With bromine; titanium tetrachloride; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jm400959q

upstream raw materials:

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

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

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

(2-furyl)methyl alcohol

Downstream raw materials:

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

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