Iloprost phenacyl ester

Base Information

• Chemical Name: Iloprost phenacyl ester
• CAS No.: 78919-13-8
• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.494
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID601333280

Synonyms:iloprost phenacyl ester;iloprost-PE

Chemical Property of Iloprost phenacyl ester

Chemical Property:

• Appearance/Colour: colorless oil
• Vapor Pressure: 7.06E-14mmHg at 25°C
• Melting Point: 115.7oC
• Refractive Index: 1.629
• Boiling Point: 539.2oC at 760 mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 294oC
• PSA: 77.76000
• Density: 1.21g/cm3
• LogP: 3.54130
• Storage Temp.: Desiccate at -20°C
• Solubility.: Soluble in methyl acetate
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 478.27192431
• Heavy Atom Count: 35
• Complexity: 837

Purity/Quality:

99%, ^*data from raw suppliers

Iloprost ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CCC(C)C(C=CC1C(CC2C1CC(=CCCCC(=O)OCC(=O)C3=CC=CC=C3)C2)O)O
• Isomeric SMILES: CC#CCC(C)C(/C=C/C1C(CC2C1C/C(=C\CCCC(=O)OCC(=O)C3=CC=CC=C3)/C2)O)O
• Description: Iloprost is a stable epoprostenol derivative which acts as an inhibitor of platelet aggregation and is recommended for the treatment of peripheral vascular diseases. The compound was shown to be a potent agonist at PGE2-sensitive and prostacyclin-sensitive receptors in animal studies. Iloprost is administered by IV infusion and has been reported to have beneficial effects in Buerger's and Raynaud's diseases as well as peripheral artery occlusive disease.
• Uses: A synthetic analogue of Prostacyclin (PGI2) used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud's phenomenon and ischemia. It acts through elevation of cAMP by binding to the prostacyclin receptor (IP receptor). Iloprost inhibits the ADP, thrombin, and collagen-induced aggregation of human platelets with an ED50 of about 13 nM. In whole animals, iloprost acts as a vasodilator, hypotensive, antidiuretic, and prolongs bleeding time.

Technology Process of Iloprost phenacyl ester

There total 52 articles about Iloprost phenacyl 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: 100.0%

Methyl (1S,5S,6R,7R)-7-Hydroxy-6-<3(R)-hydroxy-4-methyl-E-1-octen-6-ynyl>bicyclo<3.3.0>octane-E-Δ3,δ-pentanoate (101314-49-2) → 5-{(E)-(1S,5S,6R,7R)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-bicyclo[3.3.0]octa-3-ylidene)-pentanoic acid (78919-13-8)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃;

DOI:10.1248/cpb.39.309

Reference yield: 92.0%

5-[(3aS,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid (126436-91-7) → 5-{(E)-(1S,5S,6R,7R)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-bicyclo[3.3.0]octa-3-ylidene)-pentanoic acid (78919-13-8)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 30 ℃; for 12h;

Reference yield: 31.0%

C34H60O4Si2 → 5-{(E)-(1S,5S,6R,7R)-7-hydroxy-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octen-6-ynyl]-bicyclo[3.3.0]octa-3-ylidene)-pentanoic acid (78919-13-8) + 5Z-Iloprost (82889-99-4)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 30 ℃; for 12h;

DOI:10.1016/j.tetlet.2020.152627

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(3aS,4R,5R,6aR)-5-hydroxy-4-((3S,E)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl)hexahydropentalen-2(1H)-one

(3aS,4R,5R,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-((E)-(S)-3-hydroxy-4-methyl-oct-1-en-6-ynyl)-hexahydro-pentalen-2-one

Methyl (1S,5S,6R,7R)-7-Hydroxy-6-<3(R)-hydroxy-4-methyl-E-1-octen-6-ynyl>bicyclo<3.3.0>octane-E-Δ^3,δ-pentanoate

Refernces

Cross-Coupling Reaction of Alkenyl Sulfoximines and Alkenyl Aminosulfoxonium Salts with Organozincs by Dual Nickel Catalysis and Lewis Acid Promotion

10.1002/chem.201901163

The study focuses on the cross-coupling reaction (CCR) of alkenyl sulfoximines and alkenyl aminosulfoxonium salts with organozincs, facilitated by dual nickel catalysis and Lewis acid promotion. The primary chemicals utilized in this research include exocyclic, axially chiral, and acyclic alkenyl (N-methyl)sulfoximines, alkyl- and arylzincs, and Ni(dppp)Cl2 as the precatalyst. MgBr2 was employed as a promoter, and the reactions generally proceeded in ether as the solvent, although THF was also tested. The purpose of these chemicals was to investigate the CCR's effectiveness in producing stereoretentive products, which are crucial for the stereoselective synthesis of exocyclic and axially chiral alkenes. These alkenes are significant in the synthesis of medicinally important prostacyclin analogs such as iloprost, cicaprost, and inter-m-phenylene carbacyclin. The study provides insights into the stereochemical course of the CCR and its application in the synthesis of complex organic molecules with potential pharmaceutical relevance.

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