5S,6R-6-epi-Leukotriene A₄

Base Information

• Chemical Name: 5S,6R-6-epi-Leukotriene A₄
• CAS No.: 114129-56-5
• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.456
• Mol file: 114129-56-5.mol

Synonyms:

Chemical Property of 5S,6R-6-epi-Leukotriene A₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5S,6R-6-epi-Leukotriene A₄

There total 15 articles about 5S,6R-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:

C20H32O4 → 5‐oxo‐6,8,11,14‐eicosatetraenoic acid (126432-17-5,106154-18-1) + 5S,6R-6-epi-Leukotriene A4 (114129-56-5)

Guidance literature:

With recombinant Arabidopsis thaliana At-lipoxygenase1; In aq. buffer; at 0 ℃; for 0.025h; pH=6.0; Inert atmosphere; Enzymatic reaction;

DOI:10.1194/jlr.M033746

Reference yield:

C21H34O4 → 5‐oxo‐6,8,11,14‐eicosatetraenoic acid (126432-17-5,106154-18-1) + 5S,6R-6-epi-Leukotriene A4 (114129-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / methanol; dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Sonication; Heating

2: recombinant Arabidopsis thaliana At-lipoxygenase1 / aq. buffer / 0.03 h / 0 °C / pH 6.0 / Inert atmosphere; Enzymatic reaction

With recombinant Arabidopsis thaliana At-lipoxygenase1; potassium hydroxide; In methanol; dichloromethane;

DOI:10.1194/jlr.M033746

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、 Corey, E. J.,Wright, Stephen W.,Matsuda, Seiichi P. T.. "Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediate". . p. 1452 - 1455. Retrieved 2007/10/02.