(2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone

Base Information

• Chemical Name: (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone
• CAS No.: 950584-74-4
• Molecular Formula: C₂₄H₂₆OSi
• Molecular Weight: 358.555
• Mol file: 950584-74-4.mol

Synonyms:

Chemical Property of (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone

There total 4 articles about (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone 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:

1-Bromonaphthalene (90-11-9) → (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone (950584-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: t-BuLi / tetrahydrofuran; pentane / 1.17 h / -78 - 0 °C

2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: tetrahydrofuran; hexane / 2 h / -23 °C

2.3: 54 percent / p-toluenesulfonic acid / toluene / 2 h / Heating

3.1: Li; CuCN / tetrahydrofuran / -30 - 0 °C

3.2: 34 percent / tetrahydrofuran / 5.5 h / -23 - 20 °C

4.1: Chiral AD column / hexane; propan-2-ol

With chiral AD column; tert.-butyl lithium; lithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; isopropyl alcohol; pentane; 3.2: Michael addition;

DOI:10.1016/j.tet.2007.05.086

Reference yield:

2-(1-naphthyl)-2-cyclohexenone (108842-56-4) → (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone (950584-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Li; CuCN / tetrahydrofuran / -30 - 0 °C

1.2: 34 percent / tetrahydrofuran / 5.5 h / -23 - 20 °C

2.1: Chiral AD column / hexane; propan-2-ol

With chiral AD column; lithium; In tetrahydrofuran; hexane; isopropyl alcohol; 1.2: Michael addition;

DOI:10.1016/j.tet.2007.05.086

Reference yield:

naphthalen-1-yl-lithium (14474-59-0) → (2S,3S)-3-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexanone (950584-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 2 h / -23 °C

1.3: 54 percent / p-toluenesulfonic acid / toluene / 2 h / Heating

2.1: Li; CuCN / tetrahydrofuran / -30 - 0 °C

2.2: 34 percent / tetrahydrofuran / 5.5 h / -23 - 20 °C

3.1: Chiral AD column / hexane; propan-2-ol

With chiral AD column; lithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; isopropyl alcohol; 2.2: Michael addition;

DOI:10.1016/j.tet.2007.05.086

upstream raw materials:

1-Bromonaphthalene

2-(1-naphthyl)-2-cyclohexenone

naphthalen-1-yl-lithium

Downstream raw materials:

(1S,2R)-1-(dimethylphenylsilyl)-2-(1-naphthyl)cyclohexane