methyl 5-[5-hydroxy-4-[(E)-3-hydroxy-3-(4-propylcyclohexyl)prop-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl]pentanoate

Base Information

• Chemical Name: methyl 5-[5-hydroxy-4-[(E)-3-hydroxy-3-(4-propylcyclohexyl)prop-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl]pentanoate
• CAS No.: 72520-05-9
• Molecular Formula: C₂₅H₄₁NO₄
• Molecular Weight: 419.605
• Mol file: 72520-05-9.mol

Synonyms:15-(4-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-9,6-nitrilo-PGF1 methyl ester;OP 2507;OP-2507

Chemical Property of methyl 5-[5-hydroxy-4-[(E)-3-hydroxy-3-(4-propylcyclohexyl)prop-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl]pentanoate

Chemical Property:

• Vapor Pressure: 1.51E-13mmHg at 25°C
• Boiling Point: 532.2°Cat760mmHg
• Flash Point: 275.7°C
• Density: 1.19g/cm³
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 419.30355879
• Heavy Atom Count: 30
• Complexity: 608

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCC1CCC(CC1)C(C=CC2C(CC3C2CC(=N3)CCCCC(=O)OC)O)O
• Isomeric SMILES: CCCC1CCC(CC1)C(/C=C/C2C(CC3C2CC(=N3)CCCCC(=O)OC)O)O

Technology Process of methyl 5-[5-hydroxy-4-[(E)-3-hydroxy-3-(4-propylcyclohexyl)prop-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl]pentanoate

There total 11 articles about methyl 5-[5-hydroxy-4-[(E)-3-hydroxy-3-(4-propylcyclohexyl)prop-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrol-2-yl]pentanoate 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:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → 15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-6,9α-nitriloprostaglandin F1 methyl ester (72520-05-9,101758-79-6,101758-80-9,135559-37-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

2: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

3: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

4: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

5: K₂CO₃ / methanol / 1 h / 45 °C

6: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

7: p-toluenesulfonic acid, Et₃N / methanol / 1 h / Ambient temperature

8: NaN₃, dimethylsulfoxide / 19 h / 45 °C

9: toluene / 20 h / 70 °C

With sodium azide; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1) → 15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-6,9α-nitriloprostaglandin F1 methyl ester (72520-05-9,101758-79-6,101758-80-9,135559-37-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2.5 h

2: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

3: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

4: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

5: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

6: K₂CO₃ / methanol / 1 h / 45 °C

7: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

8: p-toluenesulfonic acid, Et₃N / methanol / 1 h / Ambient temperature

9: NaN₃, dimethylsulfoxide / 19 h / 45 °C

10: toluene / 20 h / 70 °C

With n-butyllithium; sodium azide; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

Reference yield:

dimethyl 2-oxo-2-cis-(4-n-propylcyclohexyl)ethyl phosphonate (101691-28-5) → 15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-6,9α-nitriloprostaglandin F1 methyl ester (72520-05-9,101758-79-6,101758-80-9,135559-37-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

2: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

3: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

4: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

5: K₂CO₃ / methanol / 1 h / 45 °C

6: triphenylphosphine, diethyl azodicarboxylate / benzene / 2 h / Ambient temperature

7: p-toluenesulfonic acid, Et₃N / methanol / 1 h / Ambient temperature

8: NaN₃, dimethylsulfoxide / 19 h / 45 °C

9: toluene / 20 h / 70 °C

With sodium azide; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.36.1128

upstream raw materials:

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

9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether

methyl cis-4-n-propylcyclohexanecarboxylate

dimethyl 2-oxo-2-cis-(4-n-propylcyclohexyl)ethyl phosphonate