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

Base Information

• Chemical Name: (5Z,E)-16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprostaglandin F_2α 11,15αβ-bis(tetrahydropyran-2-yl ether)
• CAS No.: 73275-77-1
• Molecular Formula: C₃₁H₄₁F₃O₈
• Molecular Weight: 598.657

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

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

Chemical Property:

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

There total 1 articles about (5Z,E)-16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprostaglandin F_2α 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:

3-Carboxypropylidenetriphenylphosphorane (63129-91-9) + 2-oxo-6-syn-<3αβ-(tetrahydropyran-2-yloxy)-4-<3-(trifluoromethyl)phenoxy>-1-trans-butenyl>-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-ol (57911-04-3,79171-90-7) → (5Z,E)-16-<3-(trifluoromethyl)phenoxy>-2,3,17,18,19,20-hexanorprostaglandin F2α 11,15αβ-bis(tetrahydropyran-2-yl ether) (73275-77-1)

Guidance literature:

In dimethyl sulfoxide; at 25 ℃; for 2h; Yield given;

DOI:10.1021/jm00179a011

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) → 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

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 25 ℃; under 760 Torr;

DOI:10.1021/jm00179a011

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

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: 95 percent / CHCl₃ / 5 h / 25 °C

5: 1 N aq. HCl / tetrahydrofuran / 1 h / 45 °C

With hydrogenchloride; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; chloroform; toluene;

DOI:10.1021/jm00179a011

upstream raw materials:

3-Carboxypropylidenetriphenylphosphorane

2-oxo-6-syn-<3αβ-(tetrahydropyran-2-yloxy)-4-<3-(trifluoromethyl)phenoxy>-1-trans-butenyl>-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-ol

Downstream raw materials:

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-2,3-cis-didehydroprostaglandin F_1α 11,15αβ-bis(tetrahydropyran-2-yl ether)

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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