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

Base Information

• Chemical Name: 3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one
• CAS No.: 608146-19-6
• Molecular Formula: C₂₀H₃₂N₂O₄SSi
• Molecular Weight: 424.637

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

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

Chemical Property:

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

There total 4 articles about 3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one 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: 85.0%

3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one (608146-18-5) → 3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one (608146-19-6)

Guidance literature:

With 4-toluenesulfonyl azide; triethylamine; In dichloromethane; at 20 ℃;

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

Reference yield:

methyl (2S)-2-hydroxy-4-methylpentanoate (17392-84-6) → 3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one (608146-19-6)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; 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) → 3-(tert-butyl-dimethyl-silanyloxy)-1-diazo-5-methyl-1-(toluene-4-sulfonyl)-hexan-2-one (608146-19-6)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; 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)-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

Downstream raw materials:

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

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