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

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F_1α methyl ester
• CAS No.: 73307-36-5
• Molecular Formula: C₂₃H₂₇ClO₆
• Molecular Weight: 434.917

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F_1α 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:

(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) → (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 (73307-40-1) + 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F1α methyl ester (73307-36-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 45 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1021/jm00179a011

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) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F1α methyl ester (73307-36-5)

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:

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) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans,4,5-trans,6,7-trans-hexadehydroprostaglandin F1α methyl ester (73307-36-5)

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

upstream raw materials:

(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

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

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

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