(2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone

Base Information

• Chemical Name: (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone
• CAS No.: 944282-75-1
• Molecular Formula: C₂₁H₃₂O₃Si
• Molecular Weight: 360.569
• Mol file: 944282-75-1.mol

Synonyms:(2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone

Chemical Property of (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone

There total 6 articles about (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone 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: 88.0%

benzoic acid [(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexan-6-yl]methyl ester (1019857-45-4) → (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone (944282-75-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; methanol; at 0 ℃; for 1.5h;

DOI:10.1021/jo702635t

Reference yield: 82.0%

2,2-dimethylpropanoic acid [(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexan-6-yl]methyl ester (944282-74-0) → (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone (944282-75-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; methanol; at 0 ℃; for 5h;

DOI:10.1002/anie.200700517

Reference yield:

C21H34O4Si (944282-73-9) → (2S,4R)-2-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-4-ethenylcyclopentanone (944282-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / tetrahydrofuran / 1.5 h / 0 - 20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3: 82 percent / SmI₂ / methanol; tetrahydrofuran / 5 h / 0 °C

With pyridine; samarium diiodide; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/anie.200700517

upstream raw materials:

2,2-dimethylpropanoic acid [(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexan-6-yl]methyl ester

C₂₁H₃₄O₄Si

(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester

Downstream raw materials:

(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxylic acid methyl ester

(3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-3-ethenyl-1-cyclopentene-1-carboxaldehyde

(1R,2S,3S,5S)-5-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-α,3-diethenyl-2-(1-methylene-2-propen-1-yl)cyclopentanemethanol

(1S,3S,3aR,7aS)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-1-ethenyl-2,3,3a,4,7,7a-hexahydro-7-methylene-1H-inden-4-ol