(Z)-9-[(2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]non-7-enoic acid

Base Information

• Chemical Name: (Z)-9-[(2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]non-7-enoic acid
• CAS No.: 26198-80-1
• Molecular Formula: C₂₂H₃₆O₅
• Molecular Weight: 380.525
• Mol file: 26198-80-1.mol

Synonyms:1a,1b dihomoprostaglandin E2;1a,1b-dihomo-PGE2;1a,1b-dihomoprostaglandin E2

Chemical Property of (Z)-9-[(2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]non-7-enoic acid

Chemical Property:

• Vapor Pressure: 1.61E-14mmHg at 25°C
• Boiling Point: 552.7°Cat760mmHg
• Flash Point: 302.1°C
• PSA: 94.83000
• Density: 1.119g/cm³
• LogP: 4.03130
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 380.25627424
• Heavy Atom Count: 27
• Complexity: 497

Purity/Quality:

99% ^*data from raw suppliers

1a,1b-dihomo Prostaglandin E2 ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CC=CCCCCCC(=O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)C1C/C=C\CCCCCC(=O)O)O)O

Technology Process of (Z)-9-[(2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]non-7-enoic acid

There total 15 articles about (Z)-9-[(2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]non-7-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: 81.0%

C24H40O5 → (Z)-9-((1R,2S,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)non-7-enoic acid (26198-80-1)

Guidance literature:

With Candida antarctica lipase B; In tert-butyl methyl ether; water; at 20 ℃; for 18h; Enzymatic reaction;

DOI:10.1039/c8ob00489g

Reference yield:

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde (64091-14-1) → (Z)-9-((1R,2S,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)non-7-enoic acid (26198-80-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: trifluoromethylsulfonic anhydride; 2,6-di-tert-butyl-4-methylpyridine

2.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / -30 - 0 °C / Inert atmosphere

2.2: 8 h / 20 °C

3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C / Inert atmosphere

4.3: 20 °C / Inert atmosphere

5.1: C₂₁H₃₆BCl / tetrahydrofuran; n-heptane / 6 h / -40 - -25 °C / Inert atmosphere

6.1: 1H-imidazole / dichloromethane / 12 h / 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C / Inert atmosphere

8.1: toluene / 4.5 h / -20 - 20 °C

9.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

10.1: hydrogen fluoride / water; acetonitrile / 8 h / 20 °C

11.1: Candida antarctica lipase B / water; tert-butyl methyl ether / 18 h / 20 °C / Enzymatic reaction

With 1H-imidazole; Candida antarctica lipase B; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; dimethylsulfide borane complex; C₂₁H₃₆BCl; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; hexane; n-heptane; dichloromethane; tert-butyl methyl ether; water; toluene; acetonitrile; 9.1: |Dess-Martin Oxidation;

DOI:10.1039/c8ob00489g

Reference yield:

ethyl (Z)-9-((1R,2S,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-oxocyclopentyl)non-7-enoate → (Z)-9-((1R,2S,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)non-7-enoic acid (26198-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen fluoride / water; acetonitrile / 8 h / 20 °C

2: Candida antarctica lipase B / water; tert-butyl methyl ether / 18 h / 20 °C / Enzymatic reaction

With Candida antarctica lipase B; hydrogen fluoride; In tert-butyl methyl ether; water; acetonitrile;

DOI:10.1039/c8ob00489g

upstream raw materials:

(3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4S,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-hexahydro-cyclopenta[b]furan-4-carbaldehyde

(3aR,4S,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Refernces