3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester

Base Information

• Chemical Name: 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester
• CAS No.: 256638-29-6
• Molecular Formula: C₄₂H₄₆N₂O₉
• Molecular Weight: 722.835

Synonyms:3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester

Chemical Property of 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester

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Technology Process of 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester

There total 10 articles about 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic 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: 47.0%

(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid (145071-98-3) + 3-[2-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-ylmethylene]-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-2H-pyrrol-3-yl]-propionic acid methyl ester (256638-28-5) → 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester (256638-29-6)

Guidance literature:

With trifuran-2-yl-phosphane; triethylamine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In acetonitrile; at 50 ℃; for 18h;

DOI:10.1021/jo991503u

Reference yield:

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate (20303-31-5) → 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester (256638-29-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Br₂

1.2: 80 percent / methanol / Heating

2.1: 99 percent / H₂ / Pd/C

3.1: 80 percent / NaHCO₃; I₂ / methanol; H₂O / 0 - 20 °C

4.1: 65 percent / DDQ / CH₂Cl₂ / 0.17 h / 0 °C

5.1: 15 percent / Et₃N / Pd(Ph₃P)4 / dioxane / 17 h / 50 °C

6.1: 50 percent / TsOH / CHCl₃ / 17 h

7.1: 47 percent / tri-2-furylphosphine; Et₃N / tris(dibenzylideneacetone) dipalladium / acetonitrile / 18 h / 50 °C

With trifuran-2-yl-phosphane; hydrogen; bromine; iodine; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetonitrile; 1.1: Bromination / 1.2: Dimerization / 2.1: Hydrogenolysis / 3.1: decarboxylative iodination / 4.1: Oxidation / 5.1: Substitution / 6.1: Cyclization / 7.1: coupling;

DOI:10.1021/jo991503u

Reference yield:

dibenzyl 3,3'-bis(2-methoxycarbonylethyl)-4,4'-dimethyl-2,2'-pyrromethane-5,5'-dicarboxylate (992-36-9) → 3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-dihydro-furan-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester (256638-29-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / H₂ / Pd/C

2: 80 percent / NaHCO₃; I₂ / methanol; H₂O / 0 - 20 °C

3: 65 percent / DDQ / CH₂Cl₂ / 0.17 h / 0 °C

4: 15 percent / Et₃N / Pd(Ph₃P)4 / dioxane / 17 h / 50 °C

5: 50 percent / TsOH / CHCl₃ / 17 h

6: 47 percent / tri-2-furylphosphine; Et₃N / tris(dibenzylideneacetone) dipalladium / acetonitrile / 18 h / 50 °C

With trifuran-2-yl-phosphane; hydrogen; iodine; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetonitrile; 1: Hydrogenolysis / 2: decarboxylative iodination / 3: Oxidation / 4: Substitution / 5: Cyclization / 6: coupling;

DOI:10.1021/jo991503u

upstream raw materials:

(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid

3-[2-[5-iodo-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-ylmethylene]-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-2H-pyrrol-3-yl]-propionic acid methyl ester

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate

dibenzyl 3,3'-bis(2-methoxycarbonylethyl)-4,4'-dimethyl-2,2'-pyrromethane-5,5'-dicarboxylate

Downstream raw materials:

3-{5-[3-(1-benzyloxy-ethyl)-4-methyl-5-oxo-pyrrolidin-2-ylidenemethyl]-2-[3-(2-methoxycarbonyl-ethyl)-4-methyl-5-(3-methyl-5-oxo-4-vinyl-5H-furan-2-ylidenemethyl)-pyrrol-2-ylidenemethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester

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