Fluprostenol

Base Information

• Chemical Name: Fluprostenol
• CAS No.: 54276-17-4
• Molecular Formula: C23H29F3O6
• Molecular Weight: 458.475
• Hs Code.: 2937500000
• European Community (EC) Number: 255-029-3,690-686-3
• UNII: 358S7VUE5N,MEH3MCE8X1
• DSSTox Substance ID: DTXSID7046122
• Nikkaji Number: J238.396I
• Wikidata: Q27077691
• NCI Thesaurus Code: C76900
• Pharos Ligand ID: 88YQK93XXC63
• Metabolomics Workbench ID: 61265
• ChEMBL ID: CHEMBL1201379
• Mol file: 54276-17-4.mol

Synonyms:fluprostenol;fluprostenol monosodium salt;fluprostenol, ((1alpha(Z),2beta(1E,3R*),3alpha,5alpha)-(+-))-isomer;fluprostenol, ((1R-(1alpha(Z),2beta(1E,3R*),3alpha,5alpha))-(+-))-isomer;ICI 81,008

Chemical Property of Fluprostenol

Chemical Property:

• Boiling Point: 608.0±55.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 107.22000
• Density: 1.335±0.06 g/cm3(Predicted)
• LogP: 3.56040
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Dichloromethane, Acetonitrile
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 458.19162313
• Heavy Atom Count: 32
• Complexity: 636

Purity/Quality:

97% ^*data from raw suppliers

TravoprostAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C(C1O)C=CC(COC2=CC=CC(=C2)C(F)(F)F)O)CC=CCCCC(=O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)C/C=C\CCCC(=O)O)O
• Uses: A metabolically stable analog of Prostaglandin F2α (P838625) with potent FP receptor agonist activity. An impurity of Travoprost (T715600). Fluprostenol is a metabolically stable analog of PGF2α with potent FP receptor agonist activity. Fluprostenol is the optically active enantiomer of fluprostenol and would be expected to have twice the potency as the racemic mixture. Fluprostenol inhibits PGF2α binding to human and rat FP receptors with IC50 values of 3.5 and 7.5 nM, respectively. It is a much more potent luteolytic agent than PGF2α in rats with a minimum fully effective dose of 270 μg/kg to terminate pregnancy. It is also an effective inhibitor of rat adipose precursor differentiation in primary cultures with an IC50 of 3-10 x 10?11 M.[Cayman Chemical]

Technology Process of Fluprostenol

There total 41 articles about Fluprostenol 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: 100.0%

travoprost (340181-93-3,1563176-59-9) → (+)-fluprostenol (54276-17-4)

Guidance literature:

With sodium hydroxide; In methanol; water; for 16h;

Reference yield: 70.0%

C35H57F3O6Si2 → (+)-fluprostenol (54276-17-4)

Guidance literature:

C₃₅H₅₇F₃O₆Si₂; With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 18h;

In tetrahydrofuran; pH=6.8; Aqueous phosphate buffer;

Reference yield: 51.0%

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) + [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester (114488-91-4) → (+)-fluprostenol (54276-17-4)

Guidance literature:

[1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester; With potassium carbonate; In methanol; dichloromethane;

With diisobutylaluminium hydride; In dichloromethane; toluene;

(4-carboxybutyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; stereoselective reaction;

DOI:10.1039/d1sc03237b

upstream raw materials:

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde

C₂₄H₃₁F₃O₅Si

C₂₄H₃₃F₃O₅Si

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((R,E)-3-((tert-butyldimethylsilyl)oxy)-4-(3-(trifluoromethyl)-phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

travoprost

travoprost L-homoarginine salt

arginyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate