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

Base Information

• Chemical Name: 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F_1α 11,15αβ-bis(tetrahydropyran-2-yl ether)
• CAS No.: 73275-80-6
• Molecular Formula: C₃₃H₄₃F₃O₈
• Molecular Weight: 624.695

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

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

Chemical Property:

Purity/Quality:

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

There total 4 articles about 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F_1α 11,15αβ-bis(tetrahydropyran-2-yl ether) 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:

(5Z,E)-16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprostaglandin F2α 11,15αβ-bis(tetrahydropyran-2-yl ether) (73275-77-1) → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether) (73275-80-6)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 5percent Pd/C / methanol / 25 °C / 760 Torr

2: diethyl ether

3: 100 percent / diisobutylaluminum hydride (DIBAL) / toluene / 0.5 h / -78 °C

4: CH₂Cl₂ / 0.08 h / 25 °C

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

With n-butyllithium; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; toluene;

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-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether) (73275-80-6)

Guidance literature:

Multi-step reaction with 4 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

With n-butyllithium; diisobutylaluminium hydride; In diethyl ether; dichloromethane; toluene;

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-2,2,3,3-tetradehydroprostaglandin F1α 11,15αβ-bis(tetrahydropyran-2-yl ether) (73275-80-6)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; In dichloromethane;

DOI:10.1021/jm00179a011

upstream raw materials:

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

(5Z,E)-16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprostaglandin F_2α 11,15αβ-bis(tetrahydropyran-2-yl ether)

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

Downstream 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>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E)-(S)-3-hydroxy-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-cyclopentyl}-hept-2-enoic acid

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