Rivenprost

Base Information

• Chemical Name: Rivenprost
• CAS No.: 256382-08-8
• Molecular Formula: C24H34 O6 S
• Molecular Weight: 450.596
• UNII: 1WBO45T413
• DSSTox Substance ID: DTXSID601101764
• Nikkaji Number: J1.729.883F,J1.656.304H
• Wikidata: Q27088555
• NCI Thesaurus Code: C87384
• Pharos Ligand ID: FTH9AB21CK2R
• ChEMBL ID: CHEMBL303960
• Mol file: 256382-08-8.mol

Synonyms:AE1 734;AE1-734;methyl 7-((1R,2R,3R)-3-hydroxy-2-((E)-(3S)-3-hydroxy-4-(m-methoxymethylphenyl)-1-butenyl)-5-oxocyclopentyl)-5-thiaheptanoate;ONO-4819;ONO-AE1-734;ONO4819

Chemical Property of Rivenprost

Chemical Property:

• PSA: 118.36000
• LogP: 2.93520
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 450.20760997
• Heavy Atom Count: 31
• Complexity: 580

Purity/Quality:

≥98% ^*data from raw suppliers

Rivenprost ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC1=CC=CC(=C1)CC(C=CC2C(CC(=O)C2CCSCCCC(=O)OC)O)O
• Isomeric SMILES: COCC1=CC=CC(=C1)C[C@@H](/C=C/[C@H]2[C@@H](CC(=O)[C@@H]2CCSCCCC(=O)OC)O)O
• Recent ClinicalTrials: Therapeutic Study of ONO-4819CD for Ulcerative Colitis

Technology Process of Rivenprost

There total 25 articles about Rivenprost 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: 89.0%

methyl 4-({2-[(1R,2R,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]-oxy}-2-{(1E,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]oxy}-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl}-5-oxocyclopentyl]ethyl}sulfanyl)-butanoate (256382-36-2) → Rivenprost (256382-08-8)

Guidance literature:

With fluorosilicic acid; water; In acetonitrile; at 10 ℃; for 6h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo901497u

Reference yield: 74.2%

16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-46-4) → Rivenprost (256382-08-8)

Guidance literature:

With hydrogenchloride; In methanol; acetonitrile; at 35 ℃; for 3h;

DOI:10.1016/S0968-0896(02)00085-8

Reference yield:

methyl 4-({2-[(1R,2R,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]-oxy}-2-{(1E,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]oxy}-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl}-5-oxocyclopentyl]ethyl}sulfanyl)-butanoate (256382-36-2) → C24H32O5S (443987-99-3) + Rivenprost (256382-08-8)

Guidance literature:

With fluorosilicic acid; water; In acetonitrile; at 25 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo901497u

upstream raw materials:

methyl 4-({2-[(1R,2R,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]-oxy}-2-{(1E,3S)-3-{[dimethyl(2-methyl-2-propanyl)silyl]oxy}-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl}-5-oxocyclopentyl]ethyl}sulfanyl)-butanoate

16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde

Downstream raw materials:

11-deoxy-16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaPGE1

11-deoxy-16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaPGE1 methyl ester

C₂₄H₃₂O₅S

5-thia-16-(3-methoxymethylphenyl)methylPGE₁