LEUKOTRIENE A4 METHYL ESTER

Base Information

• Chemical Name: LEUKOTRIENE A4 METHYL ESTER
• CAS No.: 72345-92-7
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• Mol file: 72345-92-7.mol

Synonyms:Oxiranebutanoicacid, 3-(1,3,5,8-tetradecatetraenyl)-, methyl ester, [2a,3b(1E,3E,5Z,8Z)]- (9CI); Oxiranebutanoic acid,3-(1,3,5,8-tetradecatetraenyl)-, methyl ester, [2a,3b(1E,3E,5Z,8Z)]-(?à)-; (?à)-Leukotriene A4 methyl ester

Chemical Property of LEUKOTRIENE A4 METHYL ESTER

Chemical Property:

• PSA: 38.83000
• LogP: 5.29230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of LEUKOTRIENE A4 METHYL ESTER

There total 49 articles about 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:

<(3Z)-nonen-1-yl>triphenylphosphonium iodide (72297-07-5) → (+/-)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:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium / 1.) THF-HMPA, -78 deg C, 1 h

2: potassium carbonate / methanol / 3 h / 23 °C

3: triphenylphosphine / CH₂Cl₂ / 1 h / 0 °C

4: toluene / 16 h / 40 °C

5: 1.) n-butyllithium / 1.) toluene, -78 deg C, 1 h

With n-butyllithium; potassium carbonate; triphenylphosphine; In methanol; dichloromethane; toluene;

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

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:

(7E,9E,11Z,14Z)-(5R,6S)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid

(7E,9E,11Z,14Z)-(5R,6S)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid

leukotriene C1

(7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid

Refernces

• 1、 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.
• 2、 Buck, Judith C.,Ellis, Frank,North, Peter, C.. "A NOVEL STEREOSPECIFIC SYNTHESIS OF (+/-)-LEUKOTRIENE A4(LTA4),METHYL ESTER". . p. 4161 - 4162. Retrieved 2007/10/02.