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

Base Information

• Chemical Name: (3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one
• CAS No.: 852204-16-1
• Molecular Formula: C₃₃H₃₉BrFNO₃Si
• Molecular Weight: 624.665
• Mol file: 852204-16-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-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: 87.0%

(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) → (3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (852204-16-1)

Guidance literature:

(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; With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; In tert-butyl methyl ether; at 20 ℃; for 19h;

With acetic acid; In tert-butyl methyl ether; at 20 ℃;

Reference yield:

(4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one (852148-48-2) → (3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (852204-16-1)

Guidance literature:

Multi-step reaction with 4 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

4: N,O-bis-(trimethylsilyl)-acetamide / tetrabutyl ammonium fluoride / tert-butyl methyl ether / 19 h / 20 °C

With 1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; 3,3-diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole; dimethylsulfide borane complex; N-ethyl-N,N-diisopropylamine; tetrabutyl ammonium fluoride; titanium tetrachloride; In dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; toluene;

Reference yield:

2-(allyloxy)-4-bromobenzaldehyde (852204-14-9) → (3R,4S)-4-[2-(allyloxy)-4-bromophenyl]-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (852204-16-1)

Guidance literature:

Multi-step reaction with 3 steps

1: isopropyl alcohol / 16.5 h / 50 °C

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

3: N,O-bis-(trimethylsilyl)-acetamide / tetrabutyl ammonium fluoride / tert-butyl methyl ether / 19 h / 20 °C

With N,O-bis-(trimethylsilyl)-acetamide; N-ethyl-N,N-diisopropylamine; tetrabutyl ammonium fluoride; titanium tetrachloride; In dichloromethane; tert-butyl methyl ether; isopropyl alcohol;

upstream raw materials:

(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

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

2-(allyloxy)-4-bromobenzaldehyde

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

Downstream raw materials:

(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

(6S)-6-O-[tert-butyl(dimethyl)silyl]-6-C-(4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}-3'-hydroxybiphenyl-3-yl)-1,2-O-(1-methylethylidene)-α-D-glucofuranose