Cicaprost

Base Information

• Chemical Name: Cicaprost
• CAS No.: 94079-80-8
• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.477
• UNII: NE94J8CAMD
• DSSTox Substance ID: DTXSID00873211
• Nikkaji Number: J398.554G
• Wikidata: Q27076013
• NCI Thesaurus Code: C174756
• Pharos Ligand ID: CC3M6YDXWM9F
• ChEMBL ID: CHEMBL160629
• Mol file: 94079-80-8.mol

Synonyms:13,14-didehydro-16,20-dimethyl-3-oxa-18,18,19,19-tetradehydro-6-carbaprostaglandin I2;5-(7-hydroxy-6-(3-hydroxy-4-methylnona-1,6-diynyl)-bicyclo(3.3.0)octan-3-yliden)-3-oxapentanoic acid;cicaprost;cicaprost dihydrochloride;ZK 96480;ZK-96480

Chemical Property of Cicaprost

Chemical Property:

• Boiling Point: 591.1°Cat760mmHg
• PKA: 3.41±0.10(Predicted)
• Flash Point: 203.4°C
• PSA: 86.99000
• Density: 1.2g/cm³
• LogP: 2.22490
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 374.20932405
• Heavy Atom Count: 27
• Complexity: 683

Purity/Quality:

97% ^*data from raw suppliers

Cicaprost ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC#CCC(C)C(C#CC1C(CC2C1CC(=CCOCC(=O)O)C2)O)O
• Isomeric SMILES: CCC#CC[C@H](C)[C@@H](C#C[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/COCC(=O)O)/C2)O)O
• Uses: A highly potent anti-metastatic Prostacyclin (P839060) analogue.

Technology Process of Cicaprost

There total 30 articles about Cicaprost 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: 94.0%

(+)-(E,3aS,4S,5R,6aS)-{[5-hydroxy-4-((3S,4S)-3-hydroxy-4-methylnona-1,6-diynyl)-hexahydropentalen-2-yliden]ethoxy}acetic acid tert-butyl ester (597557-61-4) → cicaprost (94079-80-8,95722-07-9)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 5h;

DOI:10.1021/ja030200l

Reference yield: 86.0%

{2-[(3aS,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-nona-1,6-diynyl]-hexahydro-pentalen-(2E)-ylidene]-ethoxy}-acetic acid (99783-79-6) → cicaprost (94079-80-8,95722-07-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/jm00153a001

Reference yield: 86.0%

(1S,5S,6S,7R)-6-(2-bromo-3(S)-hydroxy-4(S)-methyl-1-nonen-6-ynyl)-7-hydroxy-(E)-3-<(4-tert-butoxycarbonyl)-3-oxabutylidene>bicyclo<3.3.0>octane (112741-42-1) → cicaprost (94079-80-8,95722-07-9)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In diethyl ether; toluene; at 55 ℃; for 48h;

DOI:10.1021/jo00241a020

upstream raw materials:

(1S,5S,6S,7R)-6-(2-bromo-3(S)-hydroxy-4(S)-methyl-1-nonen-6-ynyl)-7-hydroxy-(E)-3-<(4-tert-butoxycarbonyl)-3-oxabutylidene>bicyclo<3.3.0>octane

(+)-(E,3aS,4S,5R,6aS)-{[5-hydroxy-4-((3S,4S)-3-hydroxy-4-methylnona-1,6-diynyl)-hexahydropentalen-2-yliden]ethoxy}acetic acid tert-butyl ester

(-)-(E,3aS,4S,5R,6aS)-{5-(tert-butyldimethylsilanyloxy)-4-[(3S)-(tert-butyldimethylsilanyloxy)-(4S)-methylnona-1,6-diynyl]-hexahydropentalen-2-ylidene}ethanol

(S)-2-Methyl-hept-4-yn-1-ol

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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