16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)
• CAS No.: 62561-53-9
• Molecular Formula: C₃₈H₅₅ClO₉
• Molecular Weight: 691.302

Synonyms:16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

Chemical Property of 16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α 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-tetranorprostaglandin F_2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

There total 9 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α 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:

3,4-dihydro-2H-pyran (110-87-2) + (Z)-7-[(1R,2R,3R,5S)-2-[(E)-(R)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (62524-95-2) → 16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62561-53-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃; for 0.333333h; Yield given;

DOI:10.1021/jm00179a011

Reference yield:

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9) → 16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62561-53-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

2: NaBH₄ / methanol; tetrahydrofuran / -45 °C

3: K₂CO₃ / methanol / 1 h / 50 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00179a011

Reference yield:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → 16-(3-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62561-53-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

2: NaBH₄ / methanol; tetrahydrofuran / -45 °C

3: K₂CO₃ / methanol / 1 h / 50 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

With sodium tetrahydroborate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00179a011

upstream raw materials:

3,4-dihydro-2H-pyran

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

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

Downstream raw materials:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F_2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2-(phenylselenyl)prostaglandin F_2α 9,11,15-tris(tetrahydropyran-2-yl ether)

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F_2α

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