(1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile

Base Information

• Chemical Name: (1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile
• CAS No.: 298181-29-0
• Molecular Formula: C₂₀H₃₁NO₂SSi
• Molecular Weight: 377.623

Synonyms:(1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile

Chemical Property of (1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile

Chemical Property:

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Technology Process of (1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile

There total 1 articles about (1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile 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: 93.0%

(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-oxo-hex-2-enenitrile + C6H5S(1-)*C3H9Al*Li(1+) → (1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile (298181-29-0)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; at 0 - 22 ℃; for 8h;

DOI:10.1016/S0040-4039(00)00974-6

Reference yield:

(1R,2S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-3,3-dimethyl-5-phenylsulfanyl-cyclopentanecarbonitrile (298181-29-0) → C23H38O4Si (298181-33-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 79 percent / potassium tert-butoxide / tetrahydrofuran / 1 h / 24 °C

2.1: tetrahydrofuran / 0.5 h / -20 °C

2.2: 77 percent / aq. NH₄Cl / tetrahydrofuran / 10 h / 24 °C

3.1: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 22 °C

4.1: 31 percent / LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - 0 °C

With potassium tert-butylate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; 1.1: Elimination / 2.1: Addition / 2.2: Hydrolysis / 3.1: Etherification / 4.1: Cycloaddition;

DOI:10.1016/S0040-4039(00)00974-6

Downstream raw materials:

C₂₃H₃₈O₄Si

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