(S)-tert-Butyl 1-(tert-butyldimethylsilyloxy)-3-phenylpropan-2-ylcarbamate

Base Information

• Chemical Name: (S)-tert-Butyl 1-(tert-butyldimethylsilyloxy)-3-phenylpropan-2-ylcarbamate
• CAS No.: 207122-29-0
• Molecular Formula: C20H35NO3Si
• Molecular Weight: 365.588
• Mol file: 207122-29-0.mol

Synonyms:carbamic acid, N-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester;

Chemical Property of (S)-tert-Butyl 1-(tert-butyldimethylsilyloxy)-3-phenylpropan-2-ylcarbamate

Chemical Property:

• Vapor Pressure: 9.14E-08mmHg at 25°C
• Refractive Index: 1.482
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• PSA: 47.56000
• Density: 0.974 g/cm³
• LogP: 5.53510

Purity/Quality:

99% ^*data from raw suppliers

(S)-TERT-BUTYL 1-(TERT-BUTYLDIMETHYLSILYLOXY)-3-PHENYLPROPAN-2-YL CARBAMATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-tert-Butyl 1-(tert-butyldimethylsilyloxy)-3-phenylpropan-2-ylcarbamate

There total 7 articles about (S)-tert-Butyl 1-(tert-butyldimethylsilyloxy)-3-phenylpropan-2-ylcarbamate 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: 99.0%

(2S,3R)-1-(tert-butoxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3-phenylaziridine (198829-58-2) → (2S)-2-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-3-phenylpropane (207122-29-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4h;

DOI:10.1021/jo981140i

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-2-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-3-phenylpropane (207122-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 83 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 23 °C

3: 75 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature

4: 99 percent / hydrogen / Pd/C / ethyl acetate / 4 h

With 1H-imidazole; dmap; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo981140i

Reference yield:

(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol (125414-45-1) → (2S)-2-<(tert-butoxycarbonyl)amino>-1-<(tert-butyldimethylsilyl)oxy>-3-phenylpropane (207122-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 83 percent / triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 23 °C

3: 75 percent / sodium hydride / tetrahydrofuran / 3 h / Ambient temperature

4: 99 percent / hydrogen / Pd/C / ethyl acetate / 4 h

With 1H-imidazole; dmap; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo981140i

upstream raw materials:

[(1R,2S)-2-Bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

(2S,3R)-1-(tert-butoxycarbonyl)-2-<<(tert-butyldimethylsilyl)oxy>methyl>-3-phenylaziridine

tert-butyldimethylsilyl chloride

(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol

Downstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

N-tert-butoxycarbonyl-L-phenylalanine

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Refernces

• 1、 Medina,Moyano,Pericas,Riera. "Synthesis of N-Boc-β-aryl alanines and of N-Boc-β-methyl-β-aryl alanines by regioselective ring-opening of enantiomerically pure N-Boc- aziridines". . p. 8574 - 8578. Retrieved 2007/10/03.