7-[2-(3,3-Difluoro-4-phenoxybut-1-EN-1-YL)-3,5-dihydroxycyclopentyl]hept-5-enoic acid

Base Information

• Chemical Name: 7-[2-(3,3-Difluoro-4-phenoxybut-1-EN-1-YL)-3,5-dihydroxycyclopentyl]hept-5-enoic acid
• CAS No.: 209860-88-8
• Molecular Formula: C22H28F2O5
• Molecular Weight: 410.458
• DSSTox Substance ID: DTXSID60694020
• Mol file: 209860-88-8.mol

Synonyms:DTXSID60694020;(Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid;BCP17339;7-[2-(3,3-DIFLUORO-4-PHENOXYBUT-1-EN-1-YL)-3,5-DIHYDROXYCYCLOPENTYL]HEPT-5-ENOIC ACID

Chemical Property of 7-[2-(3,3-Difluoro-4-phenoxybut-1-EN-1-YL)-3,5-dihydroxycyclopentyl]hept-5-enoic acid

Chemical Property:

• Boiling Point: 575.9±50.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 86.99000
• Density: 1.271±0.06 g/cm3(Predicted)
• LogP: 3.81600
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 410.19048031
• Heavy Atom Count: 29
• Complexity: 557

Purity/Quality:

97% ^*data from raw suppliers

TafluprostAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1O)C=CC(COC2=CC=CC=C2)(F)F)CC=CCCCC(=O)O)O
• Uses: Tafluprost Acid is a derivative of Tafluprost (T004820), a novel prostanoid used in the treatment of glaucoma and is the first prostanoid to be released in a preservative free-formula.

Technology Process of 7-[2-(3,3-Difluoro-4-phenoxybut-1-EN-1-YL)-3,5-dihydroxycyclopentyl]hept-5-enoic acid

There total 43 articles about 7-[2-(3,3-Difluoro-4-phenoxybut-1-EN-1-YL)-3,5-dihydroxycyclopentyl]hept-5-enoic acid 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: 98.0%

2,2-bis(acetoxymethyl)propyl (5Z)-7-{(1R,2R,3R,5S)-3,5-diacetoxy-2-[(1E)-3,3-difluoro-4-(phenoxy)-but-1-enyl]cyclopentyl}hept-5-enoate → AFP-172 (209860-88-8)

Guidance literature:

With lithium hydroxide monohydrate; In methanol;

DOI:10.3390/molecules22020217

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) + (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol (209861-02-9) → AFP-172 (209860-88-8)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.2533/000942904777678073

Reference yield:

(6Z,8aR,9R,10R,11aS)-9-((E)-3,3-difluoro-4-phenoxybut-1-enyl)-2,3,4,5,8,8a,9,10,11,11a-decahydro-2-oxocyclopenta[b]oxecin-10-yl 4-phenylbenzoate → AFP-172 (209860-88-8)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 2h; Inert atmosphere;

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Downstream raw materials:

(5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide

C₂₂H₂₈F₂O₅*C₁₂H₂₃N

tafluprost