14,15-Oxido-5,8,10,12-eicosatetraenoic acid

Base Information

• Chemical Name: 14,15-Oxido-5,8,10,12-eicosatetraenoic acid
• CAS No.: 81918-96-9
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Wikipedia: Eoxin_A4
• Mol file: 81918-96-9.mol

Synonyms:14,15-leukotriene A4;14,15-oxido-5,8,10,12-eicosatetraenoic acid

Chemical Property of 14,15-Oxido-5,8,10,12-eicosatetraenoic acid

Chemical Property:

• Vapor Pressure: 1.04E-10mmHg at 25°C
• Boiling Point: 484.3°C at 760 mmHg
• Flash Point: 165.1°C
• PSA: 49.83000
• Density: 1.034g/cm³
• LogP: 5.20390
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 13
• Exact Mass: 318.21949481
• Heavy Atom Count: 23
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1C(O1)C=CC=CC=CCC=CCCCC(=O)O
• Isomeric SMILES: CCCCC[C@@H]1[C@H](O1)/C=C/C=C/C=C\C/C=C\CCCC(=O)O

Technology Process of 14,15-Oxido-5,8,10,12-eicosatetraenoic acid

There total 16 articles about 14,15-Oxido-5,8,10,12-eicosatetraenoic 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:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 14S,15S-epoxy-5Z,8Z,10E,12E-eicosatetraenoic acid (81918-96-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 55 percent / pyridine

2: 40 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

3: H₂ / 10percent Pd-C

4: (nBu)4NF, AcOH / acetic acid; tetrahydrofuran

5: 55 percent / pyridine / 18 h / 5 °C

6: 60 percent / NaOMe / methanol

7: 95 percent / Cr₂O₃, celite / pyridine; various solvent(s)

8: toluene / 70 °C

10: 1.) LiHMDS; 2.) NaHCO₃ / 1.) THF, -78 deg C, for 30 min., then 0 deg C, for 45 min.

11: 1N NaOH / methanol / 1 h / 5 °C

With chromium(III) oxide; sodium hydroxide; Celite; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydrogencarbonate; acetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid; toluene;

DOI:10.1016/S0040-4039(01)99805-3

Reference yield:

5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-2,4-diol → 14S,15S-epoxy-5Z,8Z,10E,12E-eicosatetraenoic acid (81918-96-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 40 percent / tetrahydrofuran; hexamethylphosphoric acid triamide

2: H₂ / 10percent Pd-C

3: (nBu)4NF, AcOH / acetic acid; tetrahydrofuran

4: 55 percent / pyridine / 18 h / 5 °C

5: 60 percent / NaOMe / methanol

6: 95 percent / Cr₂O₃, celite / pyridine; various solvent(s)

7: toluene / 70 °C

9: 1.) LiHMDS; 2.) NaHCO₃ / 1.) THF, -78 deg C, for 30 min., then 0 deg C, for 45 min.

10: 1N NaOH / methanol / 1 h / 5 °C

With chromium(III) oxide; sodium hydroxide; Celite; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydrogencarbonate; acetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid; toluene;

DOI:10.1016/S0040-4039(01)99805-3

Reference yield:

(Z)-(2R,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-oct-5-ene-2,3-diol (89408-78-6) → 14S,15S-epoxy-5Z,8Z,10E,12E-eicosatetraenoic acid (81918-96-9)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 10percent Pd-C

2: (nBu)4NF, AcOH / acetic acid; tetrahydrofuran

3: 55 percent / pyridine / 18 h / 5 °C

4: 60 percent / NaOMe / methanol

5: 95 percent / Cr₂O₃, celite / pyridine; various solvent(s)

6: toluene / 70 °C

8: 1.) LiHMDS; 2.) NaHCO₃ / 1.) THF, -78 deg C, for 30 min., then 0 deg C, for 45 min.

9: 1N NaOH / methanol / 1 h / 5 °C

With chromium(III) oxide; sodium hydroxide; Celite; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydrogencarbonate; acetic acid; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; acetic acid; toluene;

DOI:10.1016/S0040-4039(01)99805-3

upstream raw materials:

[(2S,3S)-3-pentyloxiran-2-yl]methanol

(14S,15S)-leukotriene A₄ methyl ester

D-2-deoxyribose

trans-4,5-epoxy-(E)-2-decenal

Refernces

• 1、 Zamboni, Robert,Milette, Suzanne,Rokach, Joshua. "THE STEREOSPECIFIC SYNTHESIS OF 14S,15S-OXIDO 5Z,8Z,10E,12E-EICOSATETRAENOIC ACID". . p. 4899 - 4902. Retrieved 2007/10/02.