(S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester

Base Information

• Chemical Name: (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester
• CAS No.: 137586-42-6
• Molecular Formula: C₂₉H₂₉FNO₇P
• Molecular Weight: 553.524

Synonyms:

Chemical Property of (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester

There total 16 articles about (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-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:

(S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester (137586-41-5) → (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester (137586-42-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1021/jm00113a019

Reference yield:

1-(benzo[1,3]dioxan-4-yl)ethanone oxime (33842-14-7) → (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester (137586-42-6)

Guidance literature:

Multi-step reaction with 8 steps

1: EtONa / ethanol / 15 h / Ambient temperature

2: EtONa / ethanol / 4.5 h / Ambient temperature

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

8: HOAc, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; ammonium acetate; tetrabutyl ammonium fluoride; sodium ethanolate; acetic acid; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1021/jm00113a019

Reference yield:

4-fluorobenzaldehyde (459-57-4) → (S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-hydroxy-butyric acid methyl ester (137586-42-6)

Guidance literature:

Multi-step reaction with 8 steps

1: EtONa / ethanol / 15 h / Ambient temperature

2: EtONa / ethanol / 4.5 h / Ambient temperature

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

8: HOAc, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; copper diacetate; oxalyl dichloride; ammonium acetate; tetrabutyl ammonium fluoride; sodium ethanolate; acetic acid; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1021/jm00113a019

upstream raw materials:

(S)-4-{[6-Benzo[1,3]dioxol-4-yl-4-(4-fluoro-phenyl)-2-isopropyl-pyridin-3-ylethynyl]-methoxy-phosphinoyl}-3-(tert-butyl-diphenyl-silanyloxy)-butyric acid methyl ester

1-(benzo[1,3]dioxan-4-yl)ethanone oxime

4-fluorobenzaldehyde

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

Downstream raw materials:

(S)-4-[[[6-(1,3-Benzodioxol-4-yl)-4-(4-fluorophenyl)-2-(1-methylethyl)-3-pyridinyl]ethynyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, dilithium salt

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