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

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)
• CAS No.: 69222-88-4
• Molecular Formula: C₃₈H₅₅ClO₉
• Molecular Weight: 691.302

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

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

Chemical Property:

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

There total 2 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranor-5,6-trans-didehydroprostaglandin F_1α methyl ester 9,11,15-tris(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: 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:

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 9,11,15-tris(tetrahydropyran-2-yl ether) (69222-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / diphenyl sulfide / methanol; benzene / 22 h / Irradiation

2: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 25 °C

With diphenyl sulfide; toluene-4-sulfonic acid; In methanol; dichloromethane; benzene;

DOI:10.1021/jm00179a011

Reference yield:

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) → (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 (69222-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 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

2: 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

With dihydrogen peroxide; lithium diisopropyl amide; In methanol; ethyl acetate;

DOI:10.1021/jm00179a011

upstream raw materials:

3,4-dihydro-2H-pyran

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

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

Downstream raw materials:

(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

(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

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

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