(R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid

Base Information

• Chemical Name: (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid
• CAS No.: 1025941-22-3
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437

Synonyms:

Chemical Property of (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid

There total 7 articles about (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic 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:

4-(4-methoxyphenyl)prop-2-yn-1-ol (37614-59-8) → (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid (1025941-22-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 84 percent / NaOH; H₂; ethylenediamine / Ni(OAc)2*4H₂O; NaBH₄ / ethanol / 72 h / 760.05 Torr

2.1: N,N-dimethylaniline / CH₂Cl₂ / 0.17 h / 0 °C

2.2: 65 percent / triethylamine / CH₂Cl₂ / 20 °C

3.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

3.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

3.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

4.1: t-BuOK / diethyl ether / 0 - 20 °C

4.2: H₂O / diethyl ether / 0.25 h / 20 °C

5.1: ethyl chloroformate; Et₃N / acetone; H₂O / 0.5 h / 0 °C

5.2: NaN₃ / H₂O; acetone / 2 h / 0 °C

5.3: toluene / 3 h / Heating

6.1: 84 percent / Bu₃SnH / (Ph₃P)4Pd / CH₂Cl₂ / Heating

7.1: 1 h / 20 °C

With sodium hydroxide; potassium tert-butylate; hydrogen; tri-n-butyl-tin hydride; chloroformic acid ethyl ester; N,N-dimethyl-aniline; ethylenediamine; triethylamine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; nickel diacetate; In diethyl ether; ethanol; dichloromethane; water; acetone; 2.2: Corey-Myers reaction / 3.2: Weinreb reaction / 5.3: Curtius reaction / 6.1: Speckamp reaction;

DOI:10.1021/jo0110698

Reference yield:

(Z)-3-(4-methoxyphenyl)prop-2-en-1-ol (173542-65-9) → (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid (1025941-22-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N,N-dimethylaniline / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 65 percent / triethylamine / CH₂Cl₂ / 20 °C

2.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

2.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

2.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

3.1: t-BuOK / diethyl ether / 0 - 20 °C

3.2: H₂O / diethyl ether / 0.25 h / 20 °C

4.1: ethyl chloroformate; Et₃N / acetone; H₂O / 0.5 h / 0 °C

4.2: NaN₃ / H₂O; acetone / 2 h / 0 °C

4.3: toluene / 3 h / Heating

5.1: 84 percent / Bu₃SnH / (Ph₃P)4Pd / CH₂Cl₂ / Heating

6.1: 1 h / 20 °C

With potassium tert-butylate; tri-n-butyl-tin hydride; chloroformic acid ethyl ester; N,N-dimethyl-aniline; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; In diethyl ether; dichloromethane; water; acetone; 1.2: Corey-Myers reaction / 2.2: Weinreb reaction / 4.3: Curtius reaction / 5.1: Speckamp reaction;

DOI:10.1021/jo0110698

Reference yield:

3-(4-methoxyphenyl)-(2Z)-propenyl diazoacetate (443149-79-9) → (R)-3-[(1S,2S,3S)-2-Formyloxymethyl-3-(4-methoxy-phenyl)-cyclopropylcarbamoyl]-5-methyl-hexanoic acid (1025941-22-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

1.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

1.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

2.1: t-BuOK / diethyl ether / 0 - 20 °C

2.2: H₂O / diethyl ether / 0.25 h / 20 °C

3.1: ethyl chloroformate; Et₃N / acetone; H₂O / 0.5 h / 0 °C

3.2: NaN₃ / H₂O; acetone / 2 h / 0 °C

3.3: toluene / 3 h / Heating

4.1: 84 percent / Bu₃SnH / (Ph₃P)4Pd / CH₂Cl₂ / Heating

5.1: 1 h / 20 °C

With potassium tert-butylate; tri-n-butyl-tin hydride; chloroformic acid ethyl ester; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; In diethyl ether; dichloromethane; water; acetone; 1.2: Weinreb reaction / 3.3: Curtius reaction / 4.1: Speckamp reaction;

DOI:10.1021/jo0110698

upstream raw materials:

formic acid

[1S-(1β,2α,3α)]-1-[(2-(R)-isobutyl-4-tert-butoxycarboxyl)butanoyl]amino-3-(4-methoxyphenyl)-2-triisopropylsilyloxymethylcyclopropane

4-(4-methoxyphenyl)prop-2-yn-1-ol

(Z)-3-(4-methoxyphenyl)prop-2-en-1-ol

Downstream raw materials:

[1S-(1α,2β,3β)]-1-(3-(R)-isobutylsuccinimido)-2-hydroxymethyl-3-(4-methoxyphenyl)cyclopropane

[1S-(1α,2β,3α)]-2-(3-(R)-isobutylsuccinimido)-3-(4-methoxyphenyl)cyclopropane carboxaldehyde

[1S-(1α,2β,3α)]-2-(3-(R)-isobutylsuccinimido)-3-(4-methoxyphenyl)cyclopropanecarboxylic acid

[1S-(1α,2β,3β)]-2-acetamido-1-(3-(R)-isobutylsuccinimido)-3-(4-methoxyphenyl)cyclopropane

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