Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybut-1-en-1-yl)cyclopentyl]hept-5-enoate

Base Information

• Chemical Name: Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybut-1-en-1-yl)cyclopentyl]hept-5-enoate
• CAS No.: 130209-78-8
• Molecular Formula: C25H36O6
• Molecular Weight: 432.55
• DSSTox Substance ID: DTXSID00693951
• Mol file: 130209-78-8.mol

Synonyms:DTXSID00693951;PD049302;Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybut-1-en-1-yl)cyclopentyl]hept-5-enoate

Chemical Property of Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybut-1-en-1-yl)cyclopentyl]hept-5-enoate

Chemical Property:

• PSA: 96.22000
• LogP: 3.40860
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 432.25118886
• Heavy Atom Count: 31
• Complexity: 566

Purity/Quality:

99% ^*data from raw suppliers

16-phenoxy tetranor Prostaglandin F2α isopropyl ester ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC=CC=C2)O)O)O

Technology Process of Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybut-1-en-1-yl)cyclopentyl]hept-5-enoate

There total 2 articles about Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-4-phenoxybut-1-en-1-yl)cyclopentyl]hept-5-enoate 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: 40.0%

2-iodo-propane (75-30-9) + (Z)-7-(2-((E)-4-phenoxy-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid (40665-67-6) → (Z)-isopropyl 7-(3,5-dihydroxy-2-((E)-3-hydroxy-4-phenoxybut-1-enyl)cyclopentyl)hept-5-enoate (130209-78-8) + (Z)-isopropyl 7-(3,5-dihydroxy-2-((E)-3-hydroxy-4-phenoxybut-1-enyl)cyclopentyl)hept-5-enoate (130209-78-8)

Guidance literature:

(Z)-7-(2-((E)-4-phenoxy-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at -5 - 25 ℃; for 0.5h; Inert atmosphere;

2-iodo-propane; In acetone; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.2174/157017811795371485

Reference yield: 40.0%

2-iodo-propane (75-30-9) + (Z)-7-(2-((E)-4-phenoxy-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid (40665-67-6) → (Z)-isopropyl 7-(3,5-dihydroxy-2-((E)-3-hydroxy-4-phenoxybut-1-enyl)cyclopentyl)hept-5-enoate (130209-78-8) + (Z)-isopropyl 7-(3,5-dihydroxy-2-((E)-3-hydroxy-4-phenoxybut-1-enyl)cyclopentyl)hept-5-enoate (130209-78-8)

Guidance literature:

(Z)-7-(2-((E)-4-phenoxy-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at -5 - 25 ℃; for 0.5h; Inert atmosphere;

2-iodo-propane; In acetone; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.2174/157017811795371485

Reference yield: 65.0%

C25H36O6 (1559057-77-0,130209-78-8) → (Z)-isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxo-4-phenoxybut-1-en-1-yl)cyclopentyl)hept-5-enoate (1559057-45-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; dichloromethane; at 25 - 40 ℃; for 11h;

upstream raw materials:

2-iodo-propane

(Z)-7-(2-((E)-4-phenoxy-3-hydroxybut-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid

Downstream raw materials:

(1S,2R,3R,4R)-4-(benzoyloxy)-3-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-2-[(2Z)-7-oxo-7-(propan-2-yloxy)hept-2-en-1-yl]cyclopentyl benzoate

(1S,2R,3R,4R)-4-[(4-bromophenyl)carbonyloxy]-3-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-2-[(2Z)-7-oxo-7-(propan-2-yloxy)hept-2-en-1-yl]cyclopentyl 4-bromobenzoate

(1S,2R,3R,4R)-3-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-4-[(4-methoxyphenyl)carbonyloxy]-2-[(2Z)-7-oxo-7-(propan-2-yloxy)hept-2-en-1-yl]cyclopentyl 4-methoxybenzoate

propan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-bis(acetyloxy)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]cyclopentyl]hept-5-enoate

Refernces