82467-14-9

Upstream product

• 85514-76-7 Triphenyl-((2E,4Z,7Z)-trideca-2,4,7-trienyl)-phosphonium; bromide 
• 101053-93-4 4-(3-Formyl-oxiranyl)-butyric acid methyl ester 
• 72297-07-5 <(3Z)-nonen-1-yl>triphenylphosphonium iodide 
• 85514-73-4 (2E,4Z,7Z)-2,4,7-tridecatrienol 
• 85514-74-5 (2E,4Z,7Z)-1-Bromo-trideca-2,4,7-triene 
• 85514-72-3 Propionic acid (2E,4Z,7Z)-trideca-2,4,7-trienyl ester 
• 75817-52-6 -triphenyl-phosphonium-bromid 
• 73958-01-7 4-[3-((E)-3-Oxo-propenyl)-oxiranyl]-butyric acid methyl ester 
• 80629-41-0 methyl ester of 5(S)-hydroperoxy-6(E)-8,11,14(Z)-eicosatetranoic acid 
• 85514-75-6 diethyl 2E,4Z,7Z,tridecatrienylphosphonate 
• 89408-62-8 4-[3-((2Z,5Z,8Z)-1-Methanesulfonyloxy-tetradeca-2,5,8-trienyl)-oxiranyl]-butyric acid methyl ester 
• 73958-09-5 Phosphorane of (Z)-3-nonen-1-yl-triphenylphosponium bromide 
• 73958-00-6 4-[(2S,3R)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester 
• 63753-78-6 C₃₀H₂₈O₉ 

Downstream Products

• 73466-14-5 (7E,9E,11Z,14Z)-(5S,6R)-6-[(R)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 79026-72-5 (5R,6S)-LTC₄ 
• 73958-10-8 (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 methyl ester 
• 89461-64-3 7Z,9E,11E,14Z-LTE₄ methyl ester 
• 91944-21-7 7Z,9E,11E,14Z-LTD₄ methyl ester 
• 73836-78-9 7Z,9E,11E,14Z-LTD₄ 
• 75443-89-9 7Z,9E,11E,14Z-LTE₄ 
• 72025-60-6 (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 
• 72025-60-6 leukotriene C1 
• 72025-60-6 5(S)-hydroxy-6(R)-glutathionyl-7,9-E-11,14-Z-eicosatetraenoic acid 
• 72025-60-6 leukotriene C4 
• 72025-60-6 (7E,9Z,11Z,14Z)-(5S,6R)-6-[(S)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 72025-60-6 (7E,9Z,11Z,14Z)-(5R,6S)-6-[(S)-2-((S)-4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 

Relevant academic research and scientific papers

AN EFFICIENT AND SIMPLE METHOD THE CONVERSION OF 15-HPETE TO 14,15-EPETE (LIPOTRIENE A) AND 5-HPETE TO LEUKOTRIENE A AS THE METHYL ESTERS

Simple new methodology is described for the synthesis from arachidonic acid of the important eicosanoids lipotriene A methyl ester (5) and leukotriene A methyl ester (10), a key feature being the use of a novel chemical method for effecting the allylic hydroperoxide oxiranyl carbinol rearrangement.

CHEMICAL CONVERSION OF ARACHIDONIC ACID TO SLOW REACTING SUBSTANCES

The synthesis of slow reacting substances, leukotrienes C, D, and E, can be accomplished conveniently by a stereoselective biomimetic route.Details are provided for the conversion of 5-HPETE methyl ester 4 to leukotriene methyl ester (2) and thence to leukotrienes C and D.

A NOVEL STEREOSPECIFIC SYNTHESIS OF (+/-)-LEUKOTRIENE A4(LTA4),METHYL ESTER

The reaction of the phosphonate 1 with the epoxyaldehyde 2 is reported as the key step in a novel stereospecific synthesis of (+/-)-LTA4, methyl ester 3.

SYNTHESIS OF THE 7-CIS ISOMER OF THE NATURAL LEUKOTRIENE D4

Methyl 5(S),6(S)-oxido-11-oxo-7-cis-9-trans-undecadienoate 5 was prepared and used for the synthesis of the novel 7-cis-LTD4 (9) as well as, after isomerization to the all-trans dienal ester 3, for that of the natural leukotrienes.

SYNTHESIS, SEPARATION AND N.M.R. SPECTRA OF THREE DOUBLE BOND ISOMERS OF LEUKOTRIENE A METHYL ESTER

The synthesis and h.p.l.c. separation of three double bond isomers of leukotriene A methyl ester is described, their stereochemistry being assigned by 1H N.M.R.

CONVERGENT SYNTHESIS OF LEUKOTRIENE A METHYL ESTER

A convergent total synthesis of methyl 5,6-oxido-6,9,11,14-eicosapentaenoate from oct-2-yn-1-ol and methyl 4-formylbutyrate is described.