5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone

Base Information

• Chemical Name: 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone
• CAS No.: 608146-20-9
• Molecular Formula: C₂₀H₃₂O₄SSi
• Molecular Weight: 396.623
• Mol file: 608146-20-9.mol

Synonyms:5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone

Chemical Property of 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone

There total 5 articles about 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone 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: 77.0%

3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one (608146-19-6) → 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone (608146-20-9)

Guidance literature:

With dirhodium tetraacetate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(03)01619-8

Reference yield:

methyl (2S)-2-hydroxy-4-methylpentanoate (17392-84-6) → 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone (608146-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / imidazole; Et₃N / CH₂Cl₂ / 20 °C

2: 81 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

3: 85 percent / TsN₃; Et₃N / CH₂Cl₂ / 20 °C

4: 77 percent / Rh₂(OAc)4 / CH₂Cl₂ / 20 °C

With 1H-imidazole; dirhodium tetraacetate; n-butyllithium; 4-toluenesulfonyl azide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(03)01619-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-2-(toluene-4-sulfonyl)-cyclopentanone (608146-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / imidazole; Et₃N / CH₂Cl₂ / 20 °C

2: 81 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

3: 85 percent / TsN₃; Et₃N / CH₂Cl₂ / 20 °C

4: 77 percent / Rh₂(OAc)4 / CH₂Cl₂ / 20 °C

With 1H-imidazole; dirhodium tetraacetate; n-butyllithium; 4-toluenesulfonyl azide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(03)01619-8

upstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one

methyl (2S)-2-hydroxy-4-methylpentanoate

tert-butyldimethylsilyl chloride

2-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanoic acid methyl ester