6-epi-Leukotriene A₄

Base Information

• Chemical Name: 6-epi-Leukotriene A₄
• CAS No.: 71548-17-9
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Mol file: 71548-17-9.mol

Synonyms:

Chemical Property of 6-epi-Leukotriene A₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-epi-Leukotriene A₄

There total 11 articles about 6-epi-Leukotriene A₄ 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: 50.0%

rac-trans-(2E,4E)-3-(1,3-tetradecadiene-5,8-diynyl)oxiranebutanoic acid methyl ester (74448-21-8,74497-08-8,81075-82-3,81075-83-4,118333-86-1,118333-88-3) → (+/-)-LTA (71548-17-9,72059-45-1,74497-09-9,76375-76-3,77341-35-6,114129-55-4,114129-56-5,114129-57-6)

Guidance literature:

With hydrogen; Lindlar's catalyst; In hexane;

DOI:10.1021/ja00536a066

Reference yield:

5(S)-HPETE (71774-08-8) → 6-epi-Leukotriene A4 (71548-17-9,72059-45-1,74497-09-9,76375-76-3,77341-35-6,114129-55-4,114129-56-5,114129-57-6)

Guidance literature:

potato 5-S LO; In ethanol; at 25 ℃; for 0.75h; pH 8.0 buffer;

DOI:10.1021/ja00186a046

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 6-epi-Leukotriene A4 (71548-17-9,72059-45-1,74497-09-9,76375-76-3,77341-35-6,114129-55-4,114129-56-5,114129-57-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 1 M potassium carbonate, 2.) O₂ / 2.) potato lipoxygenase / 1.) CH₃OH, 2.) 60 atm, 4 min

2: coral 8-R-LO / ethanol / 0.75 h / 25 °C / pH 8.0 buffer

With oxygen; potassium carbonate; coral 8-R-LO; potato lipoxygenase; In ethanol;

DOI:10.1021/ja00186a046

upstream raw materials:

rac-trans-(2E,4E)-3-(1,3-tetradecadiene-5,8-diynyl)oxiranebutanoic acid methyl ester

1-bromooct-2-yne

rac-(E)-4-methyl-3,5-dioxa-7-decen-9-yne

(E)-2-tridecene-4,7-diyn-1-ol

Downstream raw materials:

Leukotriene A₄ methyl ester

5S,6R-6-epi-Leukotriene A₄ methyl ester

5R,6S-6-epi-Leukotriene A₄ methyl ester

5-epi-6-epi-leukotriene A₄ methyl ester

Refernces

• 1、 Rosenberger, Michael,Neukom, Christian. "Total Synthesis of (5R,6R,7E,9E,11Z,14Z)-5-Hydroxy-6--7,9,11,14-eicosatetraenoic Acid, a Potent SRS-A". . p. 5425 - 5426. Retrieved 2007/10/02.