(S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

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Chemical Name:(S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid
CAS No.:565452-55-3
Molecular Formula:C₃₀H₄₅N₃O₃Si
Molecular Weight:523.791
Hs Code.:

Synonyms:(S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

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Chemical Property of (S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

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Technology Process of (S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

There total 15 articles about (S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid 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%

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

: 565452-55-3
(S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; for 2.5h;
DOI:10.1021/jm0301181

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 565452-55-3
(S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

Guidance literature:: Multi-step reaction with 11 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

11.1: 83 percent / H₂O₂; aq. LiOH / tetrahydrofuran / 2.5 h

With pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; n-butyllithium; hydrogen; dihydrogen peroxide; 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

: 565452-55-3
(S)-2-azido-3-{4-[3-isopropyl-4-(triisopropylsilyloxy)benzyl]-3,5-dimethylphenyl}propionic acid

Guidance literature:: Multi-step reaction with 12 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

12.1: 83 percent / H₂O₂; aq. LiOH / tetrahydrofuran / 2.5 h

With pyridine; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; n-butyllithium; hydrogen; dihydrogen peroxide; 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