16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester
• CAS No.: 69222-87-3
• Molecular Formula: C₂₃H₃₁ClO₆
• Molecular Weight: 438.949

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

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

Chemical Property:

Purity/Quality:

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

There total 1 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin 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: 61.0%

methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate (56687-85-5) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F1α methyl ester (69222-87-3)

Guidance literature:

With diphenyl sulfide; In methanol; benzene; for 22h; Irradiation;

DOI:10.1021/jm00179a011

Reference yield: 95.0%

3,4-dihydro-2H-pyran (110-87-2) + 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F1α methyl ester (69222-87-3) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (69222-88-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃; for 0.25h;

DOI:10.1021/jm00179a011

Reference yield:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F1α methyl ester (69222-87-3) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-5,6-trans-tetradehydroprostaglandin F1α methyl ester (68399-12-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 25 °C

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

3: 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

4: 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

With dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00179a011

upstream raw materials:

methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate

Downstream raw materials:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

(2E,5E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hepta-2,5-dienoic acid methyl ester

(E)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3,5-bis-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-2-phenylselanyl-hept-5-enoic acid methyl ester

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

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