methyl (E)-4-fluoro-7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-4-enoate

Base Information

• Chemical Name: methyl (E)-4-fluoro-7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-4-enoate
• CAS No.: 109976-45-6
• Molecular Formula: C₂₂H₃₅FO₅
• Molecular Weight: 398.515
• Mol file: 109976-45-6.mol

Synonyms:4-fluoroenisoprost;4-fluoroenisoprost, (R)-isomer

Chemical Property of methyl (E)-4-fluoro-7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-4-enoate

Chemical Property:

• Vapor Pressure: 6.08E-12mmHg at 25°C
• Boiling Point: 496.6°Cat760mmHg
• Flash Point: 254.1°C
• PSA: 83.83000
• Density: 1.126g/cm³
• LogP: 4.02680
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 398.24685237
• Heavy Atom Count: 28
• Complexity: 571

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C)(CC=CC1C(CC(=O)C1CCC=C(CCC(=O)OC)F)O)O
• Isomeric SMILES: CCCC[C@@](C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CC/C=C(\CCC(=O)OC)/F)O)O

Technology Process of methyl (E)-4-fluoro-7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-4-enoate

There total 26 articles about methyl (E)-4-fluoro-7-[(1R,2R,3R)-3-hydroxy-2-[(E,4S)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]hept-4-enoate 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%

(+/-)-methyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-fluoro-16-methyl-11α-<(trimethylsilyl)oxy>-16-<(trimethylsilyl)oxy>prosta-4(E),8,13(E)-trien-1-oate (109976-43-4) → (+/-)-methyl 4-fluoro-11α,16-dihydroxy-16-methyl-9-oxoprosta-4(E),13(E)-dien-1-oate (109976-44-5,109976-45-6) + (E)-4-Fluoro-7-[(1R,2S,3S)-3-hydroxy-2-((E)-4-hydroxy-4-methyl-oct-1-enyl)-5-oxo-cyclopentyl]-hept-4-enoic acid methyl ester (109976-44-5,109976-45-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1021/jm00394a004

Reference yield: 71.0%

(+/-)-methyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-fluoro-16-methyl-11α-<(trimethylsilyl)oxy>-16-<(trimethylsilyl)oxy>prosta-4(E),8,13(E)-trien-1-oate (109976-43-4) → (+/-)-methyl 4-fluoro-11α,16-dihydroxy-16-methyl-9-oxoprosta-4(E),13(E)-dien-1-oate (109976-44-5,109976-45-6) + (E)-4-Fluoro-7-[(1R,2S,3S)-3-hydroxy-2-((E)-4-hydroxy-4-methyl-oct-1-enyl)-5-oxo-cyclopentyl]-hept-4-enoic acid methyl ester (109976-44-5,109976-45-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1021/jm00394a004

Reference yield:

furfural (98-01-1) → (+/-)-methyl 4-fluoro-11α,16-dihydroxy-16-methyl-9-oxoprosta-4(E),13(E)-dien-1-oate (109976-44-5,109976-45-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Mg, I₂, HgCl₂ / 1.) THF, RT, 1 h, 2.) THF, RT, 30 min

2: 30 percent / aq. HCl / acetone / 28 h / Ambient temperature

3: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, -40 deg C, 30 min

4: 27 percent / ZnCl₂ / dioxane; H₂O / 32 h

5: 99 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

6: 1.) n-BuLi, 2.) pentynylcopper, hexamethylphosphorous triamide / 1.) hexane, THF, -60 deg C, 90 min, 2.) THF, ether, -60 deg C, 45 min

7: hexamethylphosphoric triamide / diethyl ether / 0.75 h / -15 °C

8: 76 percent / LAH / tetrahydrofuran / 0.5 h / 0 °C

9: pyridine / 0.5 h / 0 °C

10: NaI / acetone / 1.25 h / Ambient temperature

11: 1.) lithium isopropylcyclohexylamide (LICA) / 1.) hexane, THF, -60 deg C, 30 min, 2.) hexane, THF, -60 deg C, 1 h

12: 71 percent / AcOH / tetrahydrofuran; H₂O / Ambient temperature

With pyridine; 1H-imidazole; 1-pentynyl copper; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; iodine; sodium hydride; lithium cyclohexylisopropylamide; magnesium; acetic acid; sodium iodide; mercury dichloride; zinc(II) chloride; Hexamethylphosphorous triamide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00394a004

upstream raw materials:

(+/-)-methyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-fluoro-16-methyl-11α-<(trimethylsilyl)oxy>-16-<(trimethylsilyl)oxy>prosta-4(E),8,13(E)-trien-1-oate

furfural

(E)-trimethyl[[1-methyl-1-[3-(tributylstannyl)-2-propenyl]pentyl]oxy]silane

2-hydroxy-5-(2-furyl)tetrahydrofuran