16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α

Base Information

• Chemical Name: 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α
• CAS No.: 64820-19-5
• Molecular Formula: C₂₃H₂₉F₃O₆
• Molecular Weight: 458.475

Synonyms:16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α

Chemical Property of 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α

Chemical Property:

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Technology Process of 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α

There total 7 articles about 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α 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:

2α-(6,6-dibromo-5-hexenyl)-3β-<4-<3-(trifluoromethyl)phenoxy>-3αβ-(tetrahydropyran-2-yloxy)-1-trans-butenyl>-4α-(tetrahydropyran-2-yloxy)cyclopentan-1-ol (73287-72-6) → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F1α (64820-19-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 5 h

2: 76 percent / H₂, pyridine / Pd/BaSO₄ / methanol

3: 1 N aq. HCl / tetrahydrofuran / 1.5 h / 45 °C

With pyridine; hydrogenchloride; n-butyllithium; hydrogen; Pd-BaSO₄; In tetrahydrofuran; methanol;

DOI:10.1021/jm00179a011

Reference yield:

16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprost-13-en-1-al 11,15αβ-bis(tetrahydropyran-2-yl ether) (61903-05-7) → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F1α (64820-19-5)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 0.08 h / 25 °C

2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 5 h

3: 76 percent / H₂, pyridine / Pd/BaSO₄ / methanol

4: 1 N aq. HCl / tetrahydrofuran / 1.5 h / 45 °C

With pyridine; hydrogenchloride; n-butyllithium; hydrogen; Pd-BaSO₄; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00179a011

Reference yield:

5-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-cyclopentyl}-pentanoic acid → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F1α (64820-19-5)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl ether

2: 100 percent / diisobutylaluminum hydride (DIBAL) / toluene / 0.5 h / -78 °C

3: CH₂Cl₂ / 0.08 h / 25 °C

4: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 5 h

5: 76 percent / H₂, pyridine / Pd/BaSO₄ / methanol

6: 1 N aq. HCl / tetrahydrofuran / 1.5 h / 45 °C

With pyridine; hydrogenchloride; n-butyllithium; hydrogen; diisobutylaluminium hydride; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jm00179a011

upstream raw materials:

16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α 11,15αβ-bis(tetrahydropyran-2-yl ether)

16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprost-13-en-1-al 11,15αβ-bis(tetrahydropyran-2-yl ether)

2α-(6,6-dibromo-5-hexenyl)-3β-<4-<3-(trifluoromethyl)phenoxy>-3αβ-(tetrahydropyran-2-yloxy)-1-trans-butenyl>-4α-(tetrahydropyran-2-yloxy)cyclopentan-1-ol

16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F_1α 11,15αβ-bis(tetrahydropyran-2-yl ether)

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