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

Base Information

• Chemical Name: 5-epi-6-epi-leukotriene A₄ methyl ester
• CAS No.: 79356-65-3
• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.483
• Mol file: 79356-65-3.mol

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

Chemical Property of 5-epi-6-epi-leukotriene A₄ methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-epi-6-epi-leukotriene A₄ methyl ester

There total 48 articles about 5-epi-6-epi-leukotriene A₄ methyl ester 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: 77.0%

4-[3-((2Z,5Z,8Z)-1-Methanesulfonyloxy-tetradeca-2,5,8-trienyl)-oxiranyl]-butyric acid methyl ester (89408-62-8,89461-43-8,96243-96-8,96243-97-9) → (+/-)trans-5,6-oxido-7,9-E-11,14-Z-eicosatetraenoic acid methyl ester (72297-14-4,72345-92-7,73466-12-3,73466-13-4,75879-18-4,75879-19-5,76419-95-9,76738-49-3,77210-73-2,79356-65-3,79356-68-6,80009-94-5,80629-42-1,82467-14-9,84823-27-8,84823-28-9,89461-57-4,89496-11-7,89496-12-8,92009-27-3,98102-58-0,100680-55-5)

Guidance literature:

1,8-diazabicyclo[5.4.0]undec-7-ene; at -78 - 0 ℃; for 4h;

DOI:10.1016/S0040-4039(01)81540-9

Reference yield: 34.0%

diethyl 2E,4Z,7Z,tridecatrienylphosphonate (85514-75-6) + 4-(3-Formyl-oxiranyl)-butyric acid methyl ester (101053-93-4) → (+/-)trans-5,6-oxido-7,9-E-11,14-Z-eicosatetraenoic acid methyl ester (72297-14-4,72345-92-7,73466-12-3,73466-13-4,75879-18-4,75879-19-5,76419-95-9,76738-49-3,77210-73-2,79356-65-3,79356-68-6,80009-94-5,80629-42-1,82467-14-9,84823-27-8,84823-28-9,89461-57-4,89496-11-7,89496-12-8,92009-27-3,98102-58-0,100680-55-5)

Guidance literature:

With sodium hydride; 15-crown-5; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(00)88375-6

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 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) → Leukotriene A4 methyl ester (73466-12-3) + 5S,6R-6-epi-Leukotriene A4 methyl ester (76738-49-3) + 5R,6S-6-epi-Leukotriene A4 methyl ester (79356-68-6) + 5-epi-6-epi-leukotriene A4 methyl ester (79356-65-3)

Guidance literature:

In diethyl ether; at 0 ℃; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00186a046

upstream raw materials:

Triphenyl-((2E,4Z,7Z)-trideca-2,4,7-trienyl)-phosphonium; bromide

4-(3-Formyl-oxiranyl)-butyric acid methyl ester

<(3Z)-nonen-1-yl>triphenylphosphonium iodide

(2E,4Z,7Z)-2,4,7-tridecatrienol

Downstream raw materials:

7Z,9E,11E,14Z-LTD₄

7Z,9E,11E,14Z-LTE₄

7Z,9E,11E,14Z-LTD₄ methyl ester

7Z,9E,11E,14Z-LTE₄ 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.
• 2、 Tolstikov, G. A.,Miftakhov, M. S.,Tolstikov, A. G.. "SYNTHESIS OF (+/-)-5,6-EPOXY-7E,9E,11Z,14Z-EICOSATETRAENOIC ACID METHYL ESTER". . p. 442 - 443. Retrieved 2007/10/02.