Ornoprostil

Base Information

• Chemical Name: Ornoprostil
• CAS No.: 70667-26-4
• Molecular Formula: C₂₃H₃₈O₆
• Molecular Weight: 410.551
• UNII: I4LK9LH4DJ
• ChEMBL ID: CHEMBL2107020
• DSSTox Substance ID: DTXSID901021616
• NCI Thesaurus Code: C90927
• Nikkaji Number: J23.224F
• Wikidata: Q27280441
• Mol file: 70667-26-4.mol

Synonyms:17,20-dimethyl-6-oxo-PGE1 Me ester;17,20-dimethyl-6-oxo-prostaglandin E1 methyl ester;ornoprostil;ornoprostil, (11alpha,13E,15S,17S)-isomer;OU-1308

Chemical Property of Ornoprostil

Chemical Property:

• Vapor Pressure: 2.22E-14mmHg at 25°C
• Boiling Point: 549.8°C at 760 mmHg
• PKA: 13.66±0.60(Predicted)
• Flash Point: 178.8°C
• PSA: 100.90000
• Density: 1.112g/cm³
• LogP: 3.37860
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 15
• Exact Mass: 410.26683893
• Heavy Atom Count: 29
• Complexity: 556

Purity/Quality:

98% min ^*data from raw suppliers

ORNOPROSTIL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C)CC(C=CC1C(CC(=O)C1CC(=O)CCCCC(=O)OC)O)O
• Isomeric SMILES: CCCC[C@H](C)C[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CC(=O)CCCCC(=O)OC)O)O
• Description: Omoprostil is a prostaglandin based antiulcer agent structurally related to alprostadil, enprostil and misoprostol(3). It is reportedly useful in the treatment of gastric ulcer.
• Uses: Ornoprostil is used in immunosuppressive pharmaceutical composition.

Technology Process of Ornoprostil

There total 13 articles about Ornoprostil 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: 93.0%

Ornoprostil bis-tert-butyldimethylsiloxy ether (92052-54-5) → (17S)-17,20-dimethyl-6-oxo-PGE1 methyl ester (70667-26-4,85679-51-2,92052-55-6)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In acetonitrile; for 4h; Ambient temperature;

DOI:10.1039/P19960000715

Reference yield:

6-(trimethylsilyl)hex-5-ynoic acid: (101224-43-5) → (17S)-17,20-dimethyl-6-oxo-PGE1 methyl ester (70667-26-4,85679-51-2,92052-55-6)

Guidance literature:

Multi-step reaction with 6 steps

1: conc. H₂SO₄ / 10 h / Ambient temperature

2: 1.) (c-C₆H₁₁)2BH, 2.) aq. NaOH / 2.) Pd(PPh₃)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h

3: 70percent m-CPBA / CH₂Cl₂ / 1 h / Ambient temperature

4: BF₃*Et₂O, MeOH / 0.5 h / 0 °C

5: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et₂O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

6: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature

With pyridine; methanol; sodium hydroxide; 2-thienyl(cyano)copper lithium; sulfuric acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tert.-butyl lithium; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; acetonitrile;

DOI:10.1039/P19960000715

Reference yield:

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone (117253-98-2) → (17S)-17,20-dimethyl-6-oxo-PGE1 methyl ester (70667-26-4,85679-51-2,92052-55-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / NaBr, BF₃*Et₂O / acetone / 0.5 h / Ambient temperature

2: 1.) (c-C₆H₁₁)2BH, 2.) aq. NaOH / 2.) Pd(PPh₃)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h

3: 70percent m-CPBA / CH₂Cl₂ / 1 h / Ambient temperature

4: BF₃*Et₂O, MeOH / 0.5 h / 0 °C

5: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et₂O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

6: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature

With pyridine; methanol; sodium hydroxide; 2-thienyl(cyano)copper lithium; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tert.-butyl lithium; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; acetone; acetonitrile;

DOI:10.1039/P19960000715

upstream raw materials:

Ornoprostil bis-tert-butyldimethylsiloxy ether

6-(trimethylsilyl)hex-5-ynoic acid:

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

(R)-4-(tert-Butyldimethylsiloxy)-2-(6-methoxycarbonylhexan-2-on-1-yl)cyclopent-2-enone

Refernces

• 1、 Tanaka, Toshio,Hazato, Atsuo,Bannai, Kiyoshi,Okamura, Noriaki,Sugiura, Satoshi,et al.. "Nitro-Olefin Trapping Reactions of Enolates In Situ Generated by Conjugate Addition Reaction: Short Syntheses of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1α, and PGI2". . p. 813 - 824. Retrieved 2007/10/02.