ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate

Base Information

• Chemical Name: ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate
• CAS No.: 516517-66-1
• Molecular Formula: C₄₆H₅₄O₈
• Molecular Weight: 734.93

Synonyms:ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate

Chemical Property of ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate

There total 10 articles about ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate 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: 63.0%

ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate (222555-06-8) + ethyl (E,E)-(S)-3-{4-[3-(4'-{4-hydroxybut-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate (516518-53-9) → ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate (516517-66-1)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm0309046

Reference yield:

4-Iodoacetophenone (13329-40-3) → ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate (516517-66-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaOEt / ethanol / 0.33 h

1.2: 92 percent / ethanol / 66 h / 80 °C

2.1: 100 percent / DIBAL-H / toluene; tetrahydrofuran / -15 - 20 °C

3.1: 75 percent / tetrakis(triphenylphosphine)palladium; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 18 h / 65 °C

4.1: 87 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

5.1: NaOEt / ethanol / 0.08 h

5.2: 81 percent / 24 h / 20 °C

6.1: 99 percent / DIBAL-H / toluene; tetrahydrofuran / 2.5 h / -70 - 20 °C

7.1: 76 g / azodicarboxylic dipiperidide; tributylphosphine / tetrahydrofuran / 0 - 20 °C

8.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

9.1: 63 percent / azodicarboxylic dipiperidide; tributylphosphine / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributylphosphine; tetrabutyl ammonium fluoride; sodium ethanolate; diisobutylaluminium hydride; sodium carbonate; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene; 1.2: Horner-Emmons reaction / 3.1: Suzuki reaction / 5.2: Horner-Emmons reaction / 7.1: Mitsunobu reaction / 9.1: Mitsunobu reaction;

DOI:10.1021/jm0309046

Reference yield:

4-acetylphenylboronic acid (149104-90-5) → ethyl (E,E)-(S,S)-3-{4-[3-(4'-{4-(4-(2-ethoxy-2-ethoxycarbonylethyl)phenoxy)but-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate (516517-66-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 75 percent / tetrakis(triphenylphosphine)palladium; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 18 h / 65 °C

2.1: 87 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

3.1: NaOEt / ethanol / 0.08 h

3.2: 81 percent / 24 h / 20 °C

4.1: 99 percent / DIBAL-H / toluene; tetrahydrofuran / 2.5 h / -70 - 20 °C

5.1: 76 g / azodicarboxylic dipiperidide; tributylphosphine / tetrahydrofuran / 0 - 20 °C

6.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

7.1: 63 percent / azodicarboxylic dipiperidide; tributylphosphine / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributylphosphine; tetrabutyl ammonium fluoride; sodium ethanolate; diisobutylaluminium hydride; sodium carbonate; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; toluene; 1.1: Suzuki reaction / 3.2: Horner-Emmons reaction / 5.1: Mitsunobu reaction / 7.1: Mitsunobu reaction;

DOI:10.1021/jm0309046

upstream raw materials:

ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

ethyl (E,E)-(S)-3-{4-[3-(4'-{4-hydroxybut-2-en-2-yl}biphenyl-4-yl)but-2-en-1-yloxy]phenyl}-2-ethoxypropanoate

4-Iodoacetophenone

4-acetylphenylboronic acid

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