2-Oxazolidinone, 3-[(2S)-2-azido-3-[3,5-dimethyl-4-[[3-(1-methylethyl)-4-[[tris(1-methyleth yl)silyl]oxy]phenyl]methyl]phenyl]-1-oxopropyl]-4-(phenylmethyl)-, (4S)-

Base Information

Chemical Name:2-Oxazolidinone, 3-[(2S)-2-azido-3-[3,5-dimethyl-4-[[3-(1-methylethyl)-4-[[tris(1-methyleth yl)silyl]oxy]phenyl]methyl]phenyl]-1-oxopropyl]-4-(phenylmethyl)-, (4S)-
CAS No.:565452-54-2
Molecular Formula:C40H54N4O4Si
Molecular Weight:682.979
Hs Code.:

2-Oxazolidinone,
3-[(2S)-2-azido-3-[3,5-dimethyl-4-[[3-(1-methylethyl)-4-[[tris(1-methyleth
yl)silyl]oxy]phenyl]methyl]phenyl]-1-oxopropyl]-4-(phenylmethyl)-, (4S)-

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Chemical Property of 2-Oxazolidinone, 3-[(2S)-2-azido-3-[3,5-dimethyl-4-[[3-(1-methylethyl)-4-[[tris(1-methyleth yl)silyl]oxy]phenyl]methyl]phenyl]-1-oxopropyl]-4-(phenylmethyl)-, (4S)-

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Technology Process of 2-Oxazolidinone, 3-[(2S)-2-azido-3-[3,5-dimethyl-4-[[3-(1-methylethyl)-4-[[tris(1-methyleth yl)silyl]oxy]phenyl]methyl]phenyl]-1-oxopropyl]-4-(phenylmethyl)-, (4S)-

There total 14 articles about 2-Oxazolidinone, 3-[(2S)-2-azido-3-[3,5-dimethyl-4-[[3-(1-methylethyl)-4-[[tris(1-methyleth yl)silyl]oxy]phenyl]methyl]phenyl]-1-oxopropyl]-4-(phenylmethyl)-, (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: 73.0%

: 565452-53-1
(S)-4-benzyl-3-(3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionyl)oxazolidin-2-one

: 565452-54-2
3-((S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionyl)-(S)-4-benzyloxazolidin-2-one

Guidance literature:: (S)-4-benzyl-3-(3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionyl)oxazolidin-2-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.25h;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; toluene; for 0.0125h;
DOI:10.1021/jm0301181

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 565452-54-2
3-((S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionyl)-(S)-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 72 percent / imidazole / 1,2-dichloro-ethane / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate; ethanol / 24 h / 1810.02 Torr

4.1: 99 percent / pyridine / CH₂Cl₂ / 4 h

5.1: LiCl; Cl₂Pd(PPh₃)2 / dimethylformamide / 2 h / 60 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: 86 percent / PPh₃ / CH₂Cl₂ / 0.83 h / -78 - 20 °C

7.1: 100 percent / tetrahydrofuran / Heating

8.1: 86 percent / H₂ / Pd/C / ethyl acetate; acetic acid / 20 h / 1706.59 Torr

9.1: Et₃N; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C

9.2: 89 percent / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

10.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / -78 °C

10.2: 73 percent / trisylazide / tetrahydrofuran; toluene / 0.01 h

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; hydrogen; pivaloyl chloride; potassium hexamethylsilazane; ozone; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 5.1: Stille coupling / 7.1: Wittig olefination;
DOI:10.1021/jm0301181

Reference yield:

: 7463-51-6
4-bromo-3,5-dimethylphenol

: 565452-54-2
3-((S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionyl)-(S)-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: 78 percent / K₂CO₃ / dimethylformamide / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 80 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 77 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.1: 100 percent / H₂ / Pd/C / ethyl acetate; ethanol / 24 h / 1810.02 Torr

5.1: 99 percent / pyridine / CH₂Cl₂ / 4 h

6.1: LiCl; Cl₂Pd(PPh₃)2 / dimethylformamide / 2 h / 60 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: 86 percent / PPh₃ / CH₂Cl₂ / 0.83 h / -78 - 20 °C

8.1: 100 percent / tetrahydrofuran / Heating

9.1: 86 percent / H₂ / Pd/C / ethyl acetate; acetic acid / 20 h / 1706.59 Torr

10.1: Et₃N; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C

10.2: 89 percent / tetrahydrofuran; hexane / 1 h / -78 - 20 °C

11.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.25 h / -78 °C

11.2: 73 percent / trisylazide / tetrahydrofuran; toluene / 0.01 h

With pyridine; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; hydrogen; pivaloyl chloride; potassium hexamethylsilazane; potassium carbonate; ozone; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; 6.1: Stille coupling / 8.1: Wittig olefination;
DOI:10.1021/jm0301181