(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-butyric acid methyl ester

Base Information

• Chemical Name: (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-butyric acid methyl ester
• CAS No.: 137587-08-7
• Molecular Formula: C₄₆H₅₃FNO₆PSi
• Molecular Weight: 793.988

Synonyms:

Chemical Property of (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-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-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-butyric acid methyl ester

There total 13 articles about (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-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:

4-fluorobenzaldehyde (459-57-4) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-butyric acid methyl ester (137587-08-7)

Guidance literature:

Multi-step reaction with 5 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: pyridine / 16 h / 0 °C

With piperidine; pyridine; lithium aluminium tetrahydride; copper diacetate; ammonium acetate; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; 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-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-butyric acid methyl ester (137587-08-7)

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: pyridine / 16 h / 0 °C

With pyridine; 1H-imidazole; dmap; 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

Reference yield:

(S)-4-iodo-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butanoic acid methyl ester (119673-72-2) → (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-methoxy-phosphoryl}-butyric acid methyl ester (137587-08-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / 16.5 h / 155 °C

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

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

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

5: pyridine / 16 h / 0 °C

With pyridine; bis(trimethylsilyl)trifluoroacetamide; oxalyl dichloride; trimethylsilyl bromide; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; N,N-diethyl-1,1,1-trimethylsilanamine; In dichloromethane;

DOI:10.1021/jm00113a019

upstream raw materials:

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

4-(4-fluorophenyl)-6,7-dihydro-2-(1-methylethyl)-5H-benzo[6,7]cyclohepta[1,2-b]pyridine-3-methanol

4-fluorobenzaldehyde

(S)-bromo-3-hydroxybutyric acid methyl ester

Downstream raw materials:

Sodium; (S)-4-{[4-(4-fluoro-phenyl)-2-isopropyl-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridin-3-ylmethoxy]-hydroxy-phosphoryl}-3-hydroxy-butyrate

(S)-4-[[[4-(4-Fluorophenyl)-6,7-dihydro-2-(1-methylethyl)-5H-benzo[6,7]cyclohepta [1,2-b]pyridin-3-yl]methoxy]methoxyphosphinyl]-3-hydroxybutanoic acid, methyl ester

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