Ono-AE1-437

Base Information

• Chemical Name: Ono-AE1-437
• CAS No.: 256382-23-7
• Molecular Formula: C23H32O6S
• Molecular Weight: 436.569
• UNII: T7XW73LKW4
• DSSTox Substance ID: DTXSID301102270
• Nikkaji Number: J1.579.029F
• Wikidata: Q27088195
• Pharos Ligand ID: DMLHASACJ31L
• ChEMBL ID: CHEMBL292964
• Mol file: 256382-23-7.mol

Synonyms:ONO-AE1-437;CHEMBL292964;4-[[2-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl]-5-oxocyclopentyl]ethyl]thio]butanoic acid;256382-23-7;Rivenprost free acid;D03YAS;T7XW73LKW4;GTPL8541;SCHEMBL2306273;DTXSID301102270;Butanoic acid, 4-[[2-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]-1-buten-1-yl]-5-oxocyclopentyl]ethyl]thio]-;BDBM50101858;Q27088195;16-[3-(Methoxymethyl)phenyl]-5-thia-17,18,19,20-tetranorprostaglandin E1;(8R,13E,15S)-9-Oxo-11alpha,15-dihydroxy-16-[3-(methoxymethyl)phenyl]-5-thia-17,18,19,20-tetranorprosta-13-ene-1-oic acid;4-(2-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxy-4-(3-(methoxymethyl)phenyl)but-1-enyl)-5-oxocyclopentyl)ethylthio)butanoic acid;4-(2-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-3-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethylsulfanyl)-butyric acid;4-[2-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl]-5-oxocyclopentyl]ethylsulfanyl]butanoic acid;Butanoic acid, 4-[[2-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]-1-butenyl]-5-oxocyclopentyl]ethyl]thio]-

Chemical Property of Ono-AE1-437

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 436.19195991
• Heavy Atom Count: 30
• Complexity: 566

Purity/Quality:

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)O)O)O
• Isomeric SMILES: COCC1=CC=CC(=C1)C[C@@H](/C=C/[C@H]2[C@@H](CC(=O)[C@@H]2CCSCCCC(=O)O)O)O

Technology Process of Ono-AE1-437

There total 26 articles about Ono-AE1-437 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: 91.0%

Rivenprost (256382-08-8) → 5-thia-16-(3-methoxymethylphenyl)methylPGE1 (256382-23-7)

Guidance literature:

With porcine liver esterase; In phosphate buffer; ethanol; at 20 ℃; for 1h; pH=7.4;

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

Reference yield:

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3) → 5-thia-16-(3-methoxymethylphenyl)methylPGE1 (256382-23-7)

Guidance literature:

Multi-step reaction with 12 steps

1: SO₃*Py; Et₃N / ethyl acetate; dimethylsulfoxide / 1 h / cooling

2: 83.1 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

3: LiAlH₄; (S)-BINOL / tetrahydrofuran; ethanol / 2 h / cooling

4: para-toluenesulfonic acid monohydrate / toluene; tetrahydrofuran / 0.75 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0.75 h / cooling

6: i-Pr₂NEt / tetrahydrofuran / 0.5 h / -15 - -10 °C

7: i-Pr₂NEt / tetrahydrofuran; methanol / 0.17 h / -10 - -5 °C

8: K₂CO₃ / tetrahydrofuran; methanol; dimethylformamide / 4 h / 50 °C

9: 10.5 g / K₂CO₃ / methanol / 2 h / 20 °C

10: 90.7 percent / SO₃*Py; i-Pr₂NEt / ethyl acetate; dimethylsulfoxide / 0.83 h / cooling

11: 74.2 percent / aq. HCl / acetonitrile; methanol / 3 h / 35 °C

12: 91 percent / porcine liver esterase / ethanol; aq. phosphate buffer / 1 h / 20 °C / pH 7.4

With hydrogenchloride; porcine liver esterase; lithium aluminium tetrahydride; pyridine-SO₃ complex; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; phosphate buffer; ethanol; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2: Horner-Emmons reaction;

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

Reference yield:

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde (32233-41-3) → 5-thia-16-(3-methoxymethylphenyl)methylPGE1 (256382-23-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 83.1 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

2: LiAlH₄; (S)-BINOL / tetrahydrofuran; ethanol / 2 h / cooling

3: para-toluenesulfonic acid monohydrate / toluene; tetrahydrofuran / 0.75 h / 20 °C

4: LiAlH₄ / tetrahydrofuran / 0.75 h / cooling

5: i-Pr₂NEt / tetrahydrofuran / 0.5 h / -15 - -10 °C

6: i-Pr₂NEt / tetrahydrofuran; methanol / 0.17 h / -10 - -5 °C

7: K₂CO₃ / tetrahydrofuran; methanol; dimethylformamide / 4 h / 50 °C

8: 10.5 g / K₂CO₃ / methanol / 2 h / 20 °C

9: 90.7 percent / SO₃*Py; i-Pr₂NEt / ethyl acetate; dimethylsulfoxide / 0.83 h / cooling

10: 74.2 percent / aq. HCl / acetonitrile; methanol / 3 h / 35 °C

11: 91 percent / porcine liver esterase / ethanol; aq. phosphate buffer / 1 h / 20 °C / pH 7.4

With hydrogenchloride; porcine liver esterase; lithium aluminium tetrahydride; pyridine-SO₃ complex; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; phosphate buffer; ethanol; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Horner-Emmons reaction;

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

upstream raw materials:

Rivenprost

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

16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)