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

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2-(phenylselenyl)prostaglandin F_2α 9,11,15-tris(tetrahydropyran-2-yl ether)
• CAS No.: 73287-73-7
• Molecular Formula: C₄₃H₅₇ClO₉Se
• Molecular Weight: 832.333

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

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

There total 12 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2-(phenylselenyl)prostaglandin F_2α 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: 75.0%

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-(phenylselenyl)prostaglandin F2α 9,11,15-tris(tetrahydropyran-2-yl ether) (73287-73-7)

Guidance literature:

With potassium hydroxide; In methanol; at 50 ℃; for 3h;

DOI:10.1021/jm00179a011

Reference yield:

diphenyl diselenide (1666-13-3) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2-(phenylselenyl)prostaglandin F2α 9,11,15-tris(tetrahydropyran-2-yl ether) (73287-73-7)

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: 75 percent / aq. KOH / methanol / 3 h / 50 °C

With potassium hydroxide; lithium diisopropyl amide; In methanol;

DOI:10.1021/jm00179a011

Reference yield:

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-2-(phenylselenyl)prostaglandin F2α 9,11,15-tris(tetrahydropyran-2-yl ether) (73287-73-7)

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: 75 percent / aq. KOH / methanol / 3 h / 50 °C

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

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)

diphenyl diselenide

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-2,3-trans-didehydroprostaglandin F_2α

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