(Z)-7-[(1R,2R,3R,5S)-2-(4,4-Difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-2-(4,4-Difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoic acid
• CAS No.: 136790-75-5
• Molecular Formula: C₂₅H₄₂F₂O₆
• Molecular Weight: 476.602
• Mol file: 136790-75-5.mol

Synonyms:(Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-2-(4,4-Difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoic acid

Chemical Property:

• Boiling Point: 619.5±55.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• Density: 1.16±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(1R,2R,3R,5S)-2-(4,4-Difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoic acid

There total 8 articles about (Z)-7-[(1R,2R,3R,5S)-2-(4,4-Difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]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:

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol (201341-41-5) + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (136790-75-5)

Guidance literature:

(4-carboxybutyl)triphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 - 5 ℃; for 0.5h; Inert atmosphere;

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol; In tetrahydrofuran; at 0 - 5 ℃; for 2h;

Reference yield:

(3aR,7aR,8aS)-6-(1,1-difluoropentyl)-6-hydroxyoctahydrofuro[3',2':3,4]cyclopenta[1,2-b]pyran-2(7aH)-one → (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (136790-75-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.17 h / 25 °C / Inert atmosphere

1.2: 16 h / 25 °C

2.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 2 h / -15 - -10 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 2 h / -65 - 70 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere

4.2: 2 h / 0 - 5 °C

With methanol; sodium tetrahydroborate; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (136790-73-3) → (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (136790-75-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 2 h / -15 - -10 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 2 h / -65 - 70 °C

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere

3.2: 2 h / 0 - 5 °C

With methanol; sodium tetrahydroborate; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; toluene;

upstream raw materials:

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol

(4-carboxybutyl)triphenylphosphonium bromide

Downstream raw materials:

(Z)-benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate

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