(2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester

Base Information

• Chemical Name: (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester
• CAS No.: 67039-95-6
• Molecular Formula: C₃₈H₅₁ClO₉
• Molecular Weight: 687.271

Synonyms:(2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester

Chemical Property of (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester

There total 9 articles about (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic 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:

2-oxo-7-syn-<3αβ-hydroxy-4-(3-chlorophenoxy)-1-trans-butenyl>-8-anti-hydroxy-cis-bicyclo<4.3.0>nonan-3-ol (67039-85-4) → (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester (67039-95-6)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. AgNO₃, aq. NaOH / methanol / 2 h / 25 °C

2: diethyl ether; ethyl acetate / 5 °C

3: p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 10 °C

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 40 min, b) 5 deg C, 30 min

5: 35percent H₂O₂ / ethyl acetate; tetrahydrofuran / 0.08 h / 35 °C

6: DIBAL / toluene / 0.17 h / -78 °C

7: MnO₂ / CH₂Cl₂ / 2 h / 25 °C

8: CH₂Cl₂ / 12 h / Heating

With manganese(IV) oxide; sodium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; silver nitrate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jm00179a011

Reference yield:

3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid (73319-03-6) → (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester (67039-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: diethyl ether; ethyl acetate / 5 °C

2: p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 10 °C

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 40 min, b) 5 deg C, 30 min

4: 35percent H₂O₂ / ethyl acetate; tetrahydrofuran / 0.08 h / 35 °C

5: DIBAL / toluene / 0.17 h / -78 °C

6: MnO₂ / CH₂Cl₂ / 2 h / 25 °C

7: CH₂Cl₂ / 12 h / Heating

With manganese(IV) oxide; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jm00179a011

Reference yield:

3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid methyl ester (67039-86-5,109429-57-4) → (2E,4E,6E)-7-[(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,4,6-trienoic acid methyl ester (67039-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1: p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 10 °C

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 40 min, b) 5 deg C, 30 min

3: 35percent H₂O₂ / ethyl acetate; tetrahydrofuran / 0.08 h / 35 °C

4: DIBAL / toluene / 0.17 h / -78 °C

5: MnO₂ / CH₂Cl₂ / 2 h / 25 °C

6: CH₂Cl₂ / 12 h / Heating

With manganese(IV) oxide; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

DOI:10.1021/jm00179a011

upstream raw materials:

(E)-3-methoxycarbonyl-2-propenylidenetriphenylphosphorane

1-syn,4-syn-bis(tetrahydropyran-2-yloxy)-2-syn-(2-formyl-1-trans-ethenyl)-3-anti-<3αβ-(tetrahydropyran-2-yloxy)-4-(3-chlorophenoxy)-1-trans-butenyl>cyclopentane

2-oxo-7-syn-<3αβ-hydroxy-4-(3-chlorophenoxy)-1-trans-butenyl>-8-anti-hydroxy-cis-bicyclo<4.3.0>nonan-3-ol

3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

Downstream raw materials:

(2E,4E,6E)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-hepta-2,4,6-trienoic acid methyl ester

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F_1α methyl ester

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