(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester

Base Information

• Chemical Name: (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester
• CAS No.: 137586-53-9
• Molecular Formula: C₄₄H₄₆F₂NO₅PSi
• Molecular Weight: 765.909

Synonyms:

Chemical Property of (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester

There total 16 articles about (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester 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:

2-fluoroacetophenone (450-95-3) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester (137586-53-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, 1.5 h

2: NH₄OAc, Cu(OAc)2 / acetic acid / 24 h / Heating

3: LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

4: oxalyl chloride, DMSO / CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

5: triphenylphosphine / CH₂Cl₂ / 0.42 h / Ambient temperature

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, -78 deg C, 30 min

With lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; ammonium acetate; dimethyl sulfoxide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1021/jm00113a019

Reference yield:

4-fluorobenzaldehyde (459-57-4) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester (137586-53-9)

Guidance literature:

Multi-step reaction with 7 steps

1: piperidine, HOAc / benzene / 22 h / Heating

2: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, 1.5 h

3: NH₄OAc, Cu(OAc)2 / acetic acid / 24 h / Heating

4: LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

5: oxalyl chloride, DMSO / CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

6: triphenylphosphine / CH₂Cl₂ / 0.42 h / Ambient temperature

7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, -78 deg C, 30 min

With piperidine; lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; ammonium acetate; acetic acid; dimethyl sulfoxide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetic acid; benzene;

DOI:10.1021/jm00113a019

Reference yield:

(S)-bromo-3-hydroxybutyric acid methyl ester (88759-56-2) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[5-fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-butyric acid methyl ester (137586-53-9)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole, DMAP / dimethylformamide / Ambient temperature

2: sodium iodide / butan-2-one / 5 h / Heating

3: 75 percent / 16.5 h / 155 °C

4: bis(trimethylsilyl)trifluoroacetamide (BSTFA), trimethylsilyl bromide (TMSBr) / CH₂Cl₂ / 20 h / Ambient temperature

5: dicyclohexylcarbodiimide (DCC), pyridine / 20 h / Ambient temperature

6: 1.) TMSDEA, 2.) oxalyl chloride, DMF / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, 0 deg C - 20 deg C, 1 h

7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, -78 deg C, 30 min

With pyridine; 1H-imidazole; dmap; n-butyllithium; bis(trimethylsilyl)trifluoroacetamide; oxalyl dichloride; trimethylsilyl bromide; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; N,N-diethyl-1,1,1-trimethylsilanamine; sodium iodide; In dichloromethane; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jm00113a019

upstream raw materials:

(S)-4-(Methoxychlorophosphinyl)-3-[[(t-butyl)diphenylsilyl]oxy]-butanoic acid, methyl ester

3-(2,2-Dibromoethenyl)-5-fluoro-4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenylpyridine

2-fluoroacetophenone

4-fluorobenzaldehyde

Downstream raw materials:

(S)-4-{[5-Fluoro-4-(4-fluoro-phenyl)-2-isopropyl-6-phenyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester

(S)-4-[[[5-Fluoro-4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt

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