Froxiprost

Base Information

• Chemical Name: Froxiprost
• CAS No.: 62559-74-4
• Molecular Formula: C24H29 F3 O6
• Molecular Weight: 470.48
• UNII: EOS1G6F668
• DSSTox Substance ID: DTXSID101024280
• Wikidata: Q27277273
• NCI Thesaurus Code: C90925
• ChEMBL ID: CHEMBL2107438
• Mol file: 62559-74-4.mol

Synonyms:Froxiprost;62559-74-4;Froxiprost [INN];Froxiprostum;Froxiprostum [INN-Latin];UNII-EOS1G6F668;EOS1G6F668;methyl (2E,5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hepta-2,5-dienoate;Methyl (2E,5Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-(3R)-3-hydroxy-4-((alpha,alpha,alpha-trifluoro-m-tolyl)oxy)-1-butenyl)cyclopentyl)-2,5-heptadienoate;Ono-995;FROXIPROST [JAN];SCHEMBL563113;CHEMBL2107438;REFZGTXXBBUTMJ-YDQNNXAVSA-N;DTXSID101024280;2,5-Heptadienoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, methyl ester, (1R-(1-alpha(2E,5Z),2-beta(1E,3R*),3-alpha,5-alpha))-;Q27277273;METHYL (2E,5Z)-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(3R)-3-HYDROXY-4-((.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-M-TOLYL)OXY)-1-BUTENYL)CYCLOPENTYL)-2,5-HEPTADIENOATE

Chemical Property of Froxiprost

Chemical Property:

• Vapor Pressure: 4.52E-14mmHg at 25°C
• Boiling Point: 575.2°C at 760 mmHg
• Flash Point: 301.7°C
• PSA: 96.22000
• Density: 1.298g/cm³
• LogP: 3.42480
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 470.19162313
• Heavy Atom Count: 33
• Complexity: 690

Purity/Quality:

98%Min ^*data from raw suppliers

FROXIPROST 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CCC=CCC1C(CC(C1C=CC(COC2=CC=CC(=C2)C(F)(F)F)O)O)O
• Isomeric SMILES: COC(=O)/C=C/C/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)O)O

Technology Process of Froxiprost

There total 14 articles about Froxiprost 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: 71.0%

(2E,5Z)-7-{(1R,2R,3R,5S)-3,5-Bis-(tetrahydro-pyran-2-yloxy)-2-[(E)-(R)-3-(tetrahydro-pyran-2-yloxy)-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-cyclopentyl}-hepta-2,5-dienoic acid methyl ester → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F2α methyl ester (62559-74-4)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 70 ℃; for 0.333333h;

DOI:10.1021/jm00179a011

Reference yield:

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate (54094-19-8) → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F2α methyl ester (62559-74-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

2: NaBH₄ / methanol; tetrahydrofuran / -45 °C

3: K₂CO₃ / methanol / 1 h / 50 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

6: 85 percent / 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

7: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

With sodium tetrahydroborate; dihydrogen peroxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00179a011

Reference yield:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F2α methyl ester (62559-74-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

2: NaBH₄ / methanol; tetrahydrofuran / -45 °C

3: K₂CO₃ / methanol / 1 h / 50 °C

4: p-toluenesulfonic acid / CH₂Cl₂ / 0.33 h / 25 °C

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 20 deg C, 30 min

6: 85 percent / 30percent H₂O₂ / ethyl acetate; methanol / 0.33 h / 40 °C

7: 71 percent / 65percent aq. acetic acid / tetrahydrofuran / 0.33 h / 70 °C

With sodium tetrahydroborate; dihydrogen peroxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm00179a011

upstream raw materials:

dimethyl [3-(3-(trifluoromethyl)phenoxy)-2-oxopropyl]phosphonate

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol

Downstream raw materials:

16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester

16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F_2α methyl ester

Refernces