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

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F_2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether)
• CAS No.: 62524-98-5
• Molecular Formula: C₃₈H₅₃ClO₉
• Molecular Weight: 689.286

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

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

There total 11 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin 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: 85.0%

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2-(phenylselenyl)prostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62559-75-5) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62524-98-5)

Guidance literature:

With dihydrogen peroxide; In methanol; ethyl acetate; at 40 ℃; for 0.333333h;

DOI:10.1021/jm00179a011

Reference yield:

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62524-98-5)

Guidance literature:

Multi-step reaction with 6 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

5: 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

6: 85 percent / 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

With sodium tetrahydroborate; dihydrogen peroxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

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-tetranor-2,3-trans-didehydroprostaglandin F2α methyl ester 9,11,15-tris(tetrahydropyran-2-yl ether) (62524-98-5)

Guidance literature:

Multi-step reaction with 6 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

5: 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

6: 85 percent / 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

With sodium tetrahydroborate; dihydrogen peroxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00179a011

upstream raw materials:

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

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

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

methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

Downstream raw materials:

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

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

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

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