(Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid
• CAS No.: 79740-49-1
• Molecular Formula: C₃₀H₄₉FO₇
• Molecular Weight: 540.713

Synonyms:

Chemical Property of (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid

There total 30 articles about (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid 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:

(3aS,4S,5R,6aS)-4-Fluoro-5-hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-one (61111-10-2,74643-75-7,74643-77-9,79769-12-3,79769-13-4) → (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid (79740-49-1,79740-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / p-TsOH / CH₂Cl₂ / 3 h / 0 °C

2: 100 percent / diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C

3: 1.) dimsyl sodium / 1.) DMSO, 25 deg C, 5 min, 2.) DMSO, 20 h

With diisobutylaluminium hydride; sodium methylsulfinylmethanide; toluene-4-sulfonic acid; In hexane; dichloromethane; toluene;

DOI:10.1021/jm00184a003

Reference yield:

(3,3aα,4R*,5β,6α,6aα)-hexahydro-4-fluoro-4-<3-hydroxy-1(E)-octenyl>-5-hydroxy-6-iodo-2H-cyclopentafuran-2-one (61111-09-9,74643-74-6) → (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid (79740-49-1,79740-50-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / benzene / 3 h / 50 °C

2: 70 percent / p-TsOH / CH₂Cl₂ / 3 h / 0 °C

3: 100 percent / diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C

4: 1.) dimsyl sodium / 1.) DMSO, 25 deg C, 5 min, 2.) DMSO, 20 h

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisobutylaluminium hydride; sodium methylsulfinylmethanide; toluene-4-sulfonic acid; In hexane; dichloromethane; toluene; benzene;

DOI:10.1021/jm00184a003

Reference yield:

(-)-7-fluorospirohept-5-ene-2,2'-<1,3>dioxolane>-7-methanol (71155-17-4) → (Z)-7-{(1S,2S,3R,5S)-2-Fluoro-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid (79740-49-1,79740-50-4)

Guidance literature:

Multi-step reaction with 10 steps

1: CrO₃, pyridine / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 1.) NaH / 1.) THF, 2.) THF, 52 deg C, 20 h

3: 96 percent / LiAlH₄ / diethyl ether / 0.25 h / -15 °C

4: aq. AcOH / tetrahydrofuran / 48 h / Ambient temperature

5: aq. NaOH, 30percent aq. H₂O₂ / methanol / 40 h / 5 °C

6: 50 percent / aq. NaOH, KI, aq. I₂ / 48 h / 5 °C

7: 86 percent / azobis(isobutyronitrile), tri-n-butyltin hydride / benzene / 3 h / 50 °C

8: 70 percent / p-TsOH / CH₂Cl₂ / 3 h / 0 °C

9: 100 percent / diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C

10: 1.) dimsyl sodium / 1.) DMSO, 25 deg C, 5 min, 2.) DMSO, 20 h

With pyridine; chromium(VI) oxide; sodium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; sodium methylsulfinylmethanide; toluene-4-sulfonic acid; acetic acid; potassium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; benzene;

DOI:10.1021/jm00184a003

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(3aR,4R,5S,6aR)-4-Fluoro-5-(tetrahydro-pyran-2-yloxy)-4-[(E)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-hexahydro-cyclopenta[b]furan-2-ol

(+)-5-bromo-7-fluorospiroheptane-2,2'-<1,3>dioxolane>-7-methanol

methyl (-)-(1β,4β,5β,7R^*)-5-bromo-2-oxobicyclo<2.2.1>heptane-7-carboxylate

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