(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

Base Information

Chemical Name:(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
CAS No.:73307-40-1
Molecular Formula:C₂₃H₂₇ClO₆
Molecular Weight:434.917
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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:

: 67039-95-6
(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

: 73307-40-1
(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

: 73307-36-5
16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F_1α methyl ester

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 45 ℃; for 1h; Yield given. Yields of byproduct given;
DOI:10.1021/jm00179a011

Reference yield:

: 67039-85-4
2-oxo-7-syn-<3αβ-hydroxy-4-(3-chlorophenoxy)-1-trans-butenyl>-8-anti-hydroxy-cis-bicyclo<4.3.0>nonan-3-ol

: 73307-40-1
(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

Guidance literature:: Multi-step reaction with 9 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

9: 1 N aq. HCl / tetrahydrofuran / 1 h / 45 °C

With hydrogenchloride; 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:

: 73319-03-6
3-{(1R,2R,3R,5S)-2-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-3,5-dihydroxy-cyclopentyl}-propionic acid

: 73307-40-1
(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

Guidance literature:: Multi-step reaction with 8 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

8: 1 N aq. HCl / tetrahydrofuran / 1 h / 45 °C

With hydrogenchloride; 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