(S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate

Base Information

• Chemical Name: (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate
• CAS No.: 915396-58-6
• Molecular Formula: C₂₇H₃₈O₄Si
• Molecular Weight: 454.682
• Mol file: 915396-58-6.mol

Synonyms:(S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate

Chemical Property of (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate

There total 9 articles about (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate 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: 82.0%

(S)-4-(3-(methoxy(methyl)amino)-3-oxo-2-(triethylsilyloxy)propyl)phenyl pivalate (915396-57-5) + benzylmagnesium chloride (6921-34-2) → (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate (915396-58-6)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1021/jo061395t

Reference yield:

(S)-4-(3-(2,5-dimethoxyphenyl)-2-hydroxy-3-oxopropyl)phenyl pivalate (869093-43-6) → (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate (915396-58-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / bis(trimethylsilyl)peroxide; rac-trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine; potassium carbonate / tin(IV) chloride; molecular sieves 4 Angstroem / CH₂Cl₂ / 1.25 h / 0 °C

2: 92 percent / trimethylaluminum / CH₂Cl₂; hexane / 5 h / 20 °C

3: 91 percent / imidazole / dimethylformamide / 5 h / 20 °C

4: 82 percent / tetrahydrofuran / 2.5 h / 0 °C

With 1H-imidazole; bis-trimethylsilanyl peroxide; rac-trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine; trimethylaluminum; potassium carbonate; 4 A molecular sieve; tin(IV) chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Baeyer-Villiger oxidation / 4: Grignard reaction;

DOI:10.1021/jo061395t

Reference yield:

(S)-4-(2-(benzhydryloxy)-3-(2,5-dimethoxyphenyl)-3-oxopropyl)phenyl pivalate (869093-41-4) → (S)-4-(3-oxo-4-phenyl-2-(triethylsilyloxy)butyl)phenyl pivalate (915396-58-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / titanium(IV) chloride / CH₂Cl₂ / 0.33 h / -78 °C

2: 75 percent / bis(trimethylsilyl)peroxide; rac-trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine; potassium carbonate / tin(IV) chloride; molecular sieves 4 Angstroem / CH₂Cl₂ / 1.25 h / 0 °C

3: 92 percent / trimethylaluminum / CH₂Cl₂; hexane / 5 h / 20 °C

4: 91 percent / imidazole / dimethylformamide / 5 h / 20 °C

5: 82 percent / tetrahydrofuran / 2.5 h / 0 °C

With 1H-imidazole; bis-trimethylsilanyl peroxide; rac-trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine; trimethylaluminum; titanium tetrachloride; potassium carbonate; 4 A molecular sieve; tin(IV) chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 2: Baeyer-Villiger oxidation / 5: Grignard reaction;

DOI:10.1021/jo061395t

upstream raw materials:

(S)-4-(3-(methoxy(methyl)amino)-3-oxo-2-(triethylsilyloxy)propyl)phenyl pivalate

benzylmagnesium chloride

(S)-4-(3-(2,5-dimethoxyphenyl)-2-hydroxy-3-oxopropyl)phenyl pivalate

(S)-2,5-dimethoxyphenyl 2-hydroxy-3-(4-pivaloyloxyphenyl)propanoate