(4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one
• CAS No.: 915215-36-0
• Molecular Formula: C₄₃H₅₀BrFN₂O₅Si
• Molecular Weight: 801.868
• Mol file: 915215-36-0.mol

Synonyms:(4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one

Chemical Property of (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one

There total 10 articles about (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-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: 83.0%

N-{(1E)-[2-(allyloxy)-4-bromophenyl]methylene}aniline (852148-51-7) + (4S)-4-benzyl-3-[(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-1,3-oxazolidin-2-one (852148-50-6) → (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one (915215-36-0)

Guidance literature:

N-{(1E)-[2-(allyloxy)-4-bromophenyl]methylene}aniline; (4S)-4-benzyl-3-[(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-1,3-oxazolidin-2-one; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -30 - -25 ℃;

With acetic acid; In dichloromethane; at -35 ℃; for 0.1h;

With tartaric acid; sodium sulfite; more than 3 stages;

Reference yield:

(4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one (852148-48-2) → (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one (915215-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 3,3-diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; dimethylsulfide borane complex / dichloromethane; toluene / 5.5 h / -5 °C / Cooling with methanol-dry ice

2: 1H-imidazole / N,N-dimethyl-formamide / 19 h / 20 °C

3: N-ethyl-N,N-diisopropylamine / titanium tetrachloride / dichloromethane / 3.2 h / -30 - -25 °C

With 1H-imidazole; 3,3-diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; dimethylsulfide borane complex; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

2-(allyloxy)-4-bromobenzaldehyde (852204-14-9) → (4S)-3-[(2R,5S)-2-[(S)-[2-(allyloxy)-4-bromophenyl](anilino)methyl]-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-4-benzyl-1,3-oxazolidin-2-one (915215-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: isopropyl alcohol / 16.5 h / 50 °C

2: N-ethyl-N,N-diisopropylamine / titanium tetrachloride / dichloromethane / 3.2 h / -30 - -25 °C

With N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In dichloromethane; isopropyl alcohol;

upstream raw materials:

N-{(1E)-[2-(allyloxy)-4-bromophenyl]methylene}aniline

(4S)-4-benzyl-3-[(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-5-(4-fluorophenyl)pentanoyl]-1,3-oxazolidin-2-one

(4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one

2-(allyloxy)-4-bromobenzaldehyde

Downstream raw materials:

(3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one

(3R,4S)-4-(4-bromo-2-hydroxyphenyl)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one

(3R,4S)-4-(4-bromo-2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one

(3R,4S)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-[2-{[tert-butyl(dimethyl)silyl]oxy}-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-phenylazetidin-2-one