16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester

Base Information

• Chemical Name: 16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester
• CAS No.: 64775-62-8
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.488
• Mol file: 64775-62-8.mol

Synonyms:

Chemical Property of 16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester

There total 14 articles about 16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α 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: 10.0%

16-phenoxy-17,18,19,20-tetranor-2,3-trans-didehydroprostagland (62524-94-1) → 16-phenoxy-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F2α methyl ester (64812-67-5) + 16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F2α methyl ester (64775-62-8,64812-67-5,64812-77-7,73364-95-1)

Guidance literature:

With potassium carbonate; In methanol; at 0 ℃; for 1.5h;

DOI:10.1021/jm00179a011

Reference yield:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate (40665-68-7) → 16-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F2α methyl ester (64775-62-8,64812-67-5,64812-77-7,73364-95-1)

Guidance literature:

Multi-step reaction with 8 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: 36 percent / 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

7: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

8: 10 percent / K₂CO₃ / methanol / 1.5 h / 0 °C

With sodium tetrahydroborate; dihydrogen peroxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic 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-phenoxy-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F2α methyl ester (64775-62-8,64812-67-5,64812-77-7,73364-95-1)

Guidance literature:

Multi-step reaction with 8 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: 36 percent / 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

7: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

8: 10 percent / K₂CO₃ / methanol / 1.5 h / 0 °C

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

DOI:10.1021/jm00179a011

upstream raw materials:

16-phenoxy-17,18,19,20-tetranor-2,3-trans-didehydroprostagland

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

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-phenoxy-17,18,19,20-tetranor-3,4-trans-5,6-trans-tetradehydroprostaglamdin F_1α methyl ester

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

Refernces