2-Azetidinone, 4-[4-bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-[(3S)-3-[[(1, 1-dimethylethyl)dimethylsilyl]oxy]-3-(4-fluorophenyl)propyl]-1-phenyl-, (3R,4S)-

Base Information

• Chemical Name: 2-Azetidinone, 4-[4-bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-[(3S)-3-[[(1, 1-dimethylethyl)dimethylsilyl]oxy]-3-(4-fluorophenyl)propyl]-1-phenyl-, (3R,4S)-
• CAS No.: 852204-20-7
• Molecular Formula: C36H49BrFNO3Si2
• Molecular Weight: 698.863
• Mol file: 852204-20-7.mol

Synonyms:

Chemical Property of 2-Azetidinone, 4-[4-bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-[(3S)-3-[[(1, 1-dimethylethyl)dimethylsilyl]oxy]-3-(4-fluorophenyl)propyl]-1-phenyl-, (3R,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Azetidinone, 4-[4-bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-[(3S)-3-[[(1, 1-dimethylethyl)dimethylsilyl]oxy]-3-(4-fluorophenyl)propyl]-1-phenyl-, (3R,4S)-

There total 13 articles about 2-Azetidinone, 4-[4-bromo-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-3-[(3S)-3-[[(1, 1-dimethylethyl)dimethylsilyl]oxy]-3-(4-fluorophenyl)propyl]-1-phenyl-, (3R,4S)- 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%

(3R,4S)-4-(4-bromo-2-hydroxyphenyl)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-1-phenylazetidin-2-one (852204-18-3) + t-butyldimethylsiyl triflate (69739-34-0) → (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 (852204-20-7)

Guidance literature:

With 2,6-dimethylpyridine; In DMF (N,N-dimethyl-formamide); dichloromethane; at 20 ℃; for 4.5h;

Reference yield:

(4S)-4-benzyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one (852148-48-2) → (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 (852204-20-7)

Guidance literature:

Multi-step reaction with 6 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

5: morpholine / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C

6: 2,6-dimethylpyridine / dichloromethane; N,N-dimethyl-formamide / 6.75 h / 20 °C

With morpholine; 1H-imidazole; 2,6-dimethylpyridine; 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; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; titanium tetrachloride; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; toluene;

Reference yield:

2-(allyloxy)-4-bromobenzaldehyde (852204-14-9) → (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 (852204-20-7)

Guidance literature:

Multi-step reaction with 5 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

4: morpholine / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1.5 h / 20 °C

5: 2,6-dimethylpyridine / dichloromethane; N,N-dimethyl-formamide / 6.75 h / 20 °C

With morpholine; 2,6-dimethylpyridine; N,O-bis-(trimethylsilyl)-acetamide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; titanium tetrachloride; In tetrahydrofuran; dichloromethane; tert-butyl methyl ether; N,N-dimethyl-formamide; isopropyl alcohol;

upstream 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

t-butyldimethylsiyl triflate

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

2-(allyloxy)-4-bromobenzaldehyde

Downstream raw materials:

(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

dimethyl (3'-{[tert-butyl(dimethyl)silyl]oxy}-4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)phosphonate

(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

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(3'-{[tert-butyl(dimethyl)silyl]oxy}-4'-{(2S,3R)-3-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-3-(4-fluorophenyl)propyl]-4-oxo-1-phenylazetidin-2-yl}biphenyl-3-yl)-D-glucitol