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

Base Information

• Chemical Name: (Z)-Benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate
• CAS No.: 136790-77-7
• Molecular Formula: C₃₂H₄₈F₂O₆
• Molecular Weight: 566.726
• UNII: 8QU2RN7FKE
• Mol file: 136790-77-7.mol

Synonyms:(Z)-Benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate;136790-77-7;Benzyl (Z)-7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(oxan-2-yloxy)cyclopentyl]hept-5-enoate;8QU2RN7FKE;benzyl (z)-7-[(1r,2r,3r,5s)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2h-pyran-2-yl)oxy]cyclopentyl)hept-5-enoate;Benzyl (Z)-7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoate;AC-29982;(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;(Z)-Benzyl7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate;Phenylmethyl (5Z,9alpha,11alpha)-16,16-difluoro-9,15-dihydroxy-11-[(tetrahydro-2H-pyran-2-yl)oxy]prost-5-en-1-oate;Prost-5-en-1-oic acid, 16,16-difluoro-9,15-dihydroxy-11-[(tetrahydro-2H-pyran-2-yl)oxy]-, phenylmethyl ester, (5Z,9alpha,11alpha)-

Chemical Property of (Z)-Benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate

Chemical Property:

• Boiling Point: 662.1±55.0 °C(Predicted)
• PKA: 13.90±0.20(Predicted)
• PSA: 85.22000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 6.72180
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 18
• Exact Mass: 566.34189557
• Heavy Atom Count: 40
• Complexity: 741

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC(C(CCC1C(CC(C1CC=CCCCC(=O)OCC2=CC=CC=C2)O)OC3CCCCO3)O)(F)F
• Isomeric SMILES: CCCCC(C(CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)OCC2=CC=CC=C2)O)OC3CCCCO3)O)(F)F

Technology Process of (Z)-Benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate

There total 9 articles about (Z)-Benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-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:

(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) + benzyl bromide (100-39-0) → (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 (136790-77-7)

Guidance literature:

(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; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 19 - 25 ℃; Inert atmosphere;

benzyl bromide; In acetone; at 20 - 25 ℃; for 18h;

Reference yield:

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (64927-55-5) → (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 (136790-77-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / methanol / 17 h / 25 - 35 °C / Inert atmosphere

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

2.2: 16 h / 25 °C

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

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

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

5.2: 2 h / 0 - 5 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 19 - 25 °C / Inert atmosphere

6.2: 18 h / 20 - 25 °C

With methanol; sodium tetrahydroborate; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

Reference yield:

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → (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 (136790-77-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 26 °C / Inert atmosphere

1.3: 20 h / 25 - 45 °C

2.1: pyrographite / ethyl acetate / 2 h / 25 - 40 °C

2.2: 20 - 25 °C / 1034.32 - 1292.9 Torr / Inert atmosphere

3.1: potassium carbonate / methanol / 17 h / 25 - 35 °C / Inert atmosphere

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

4.2: 16 h / 25 °C

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

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

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

7.2: 2 h / 0 - 5 °C

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 19 - 25 °C / Inert atmosphere

8.2: 18 h / 20 - 25 °C

With methanol; sodium tetrahydroborate; potassium tert-butylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyrographite; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; toluene; mineral oil;

upstream raw materials:

(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

benzyl bromide

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

(3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Refernces