methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester

Base Information

• Chemical Name: methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester
• CAS No.: 869588-27-2
• Molecular Formula: C₂₅H₁₉F₂NO₅S
• Molecular Weight: 483.492

Synonyms:methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester

Chemical Property of methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester

Chemical Property:

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Technology Process of methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester

There total 5 articles about methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl 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:

methanesulfonic acid 4-[(E)-3-hydroxyhexa-1,5-dienyl]phenyl ester → methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester (869588-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 51 percent / PPh₃; Et₃N / Pd(OAc)2 / acetonitrile / 4 h / Heating

2.1: EtMgBr; i-PrOH / CH₂Cl₂ / 0 - 23 °C

2.2: tert-butyl hypochlorite / CH₂Cl₂ / -78 - 23 °C

2.3: 36 percent / CH₂Cl₂ / 30 h / 23 °C

3.1: pyridine / CH₂Cl₂ / 16 h / 23 °C

4.1: DBU / CH₂Cl₂ / 12 h / Heating

4.2: aq. NaIO₄; K₂OsO₄ / tetrahydrofuran / 14 h

5.1: CH₂Cl₂ / 0.5 h / 23 °C

With pyridine; ethylmagnesium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; isopropyl alcohol; palladium diacetate; In dichloromethane; acetonitrile; 1.1: Heck arylation / 5.1: Wittig reaction;

DOI:10.1039/b510100j

Reference yield:

methanesulfonic acid 4-[(1E,5E)-(S)-3-hydroxy-6-phenylhexa-1,5-dienyl]phenyl ester (869588-23-8) → methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester (869588-27-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: EtMgBr; i-PrOH / CH₂Cl₂ / 0 - 23 °C

1.2: tert-butyl hypochlorite / CH₂Cl₂ / -78 - 23 °C

1.3: 36 percent / CH₂Cl₂ / 30 h / 23 °C

2.1: pyridine / CH₂Cl₂ / 16 h / 23 °C

3.1: DBU / CH₂Cl₂ / 12 h / Heating

3.2: aq. NaIO₄; K₂OsO₄ / tetrahydrofuran / 14 h

4.1: CH₂Cl₂ / 0.5 h / 23 °C

With pyridine; ethylmagnesium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; isopropyl alcohol; In dichloromethane; 4.1: Wittig reaction;

DOI:10.1039/b510100j

Reference yield:

Methanesulfonic acid (E)-(S)-1-[(4S,5S)-3-(4-fluoro-phenyl)-4-(4-methanesulfonyloxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-4-phenyl-but-3-enyl ester → methanesulfonic acid 4-{(4S,5R)-3-(4-fluorophenyl)-5-[(E)-3-(4-fluorophenyl)-3-oxopropenyl]-4,5-dihydroisoxazol-4-yl}phenyl ester (869588-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DBU / CH₂Cl₂ / 12 h / Heating

1.2: aq. NaIO₄; K₂OsO₄ / tetrahydrofuran / 14 h

2.1: CH₂Cl₂ / 0.5 h / 23 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 2.1: Wittig reaction;

DOI:10.1039/b510100j

upstream raw materials:

Methanesulfonic acid 4-[(4S,5S)-3-(4-fluoro-phenyl)-5-formyl-4,5-dihydro-isoxazol-4-yl]-phenyl ester

1-(4-fluorophenyl)-2-(triphenyl-λ⁵phosphanylidene)ethanone

methanesulfonic acid 4-[(1E,5E)-(S)-3-hydroxy-6-phenylhexa-1,5-dienyl]phenyl ester

methanesulfonic acid 4-{(4S,5S)-3-(4-fluorophenyl)-5-[(E)-(S)-1-hydroxy-4-phenylbut-3-enyl]-4,5-dihydroisoxazol-4-yl}phenyl ester

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