74841-69-3

Usage

Uses

11-trans Leukotriene C4 is a C-11 double bond isomer of LTC4.

InChI:InChI=1/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9+,12-11+,16-13+/t22-,23-,24-,25+/m0/s1

Upstream product

• 75415-33-7 (7E,9E,11Z,14Z)-5-Hydroxy-6-{2-(methoxycarbonylmethyl-carbamoyl)-2-[4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester 
• 75415-33-7 (7E,9E,11Z,14Z)-(5S,6R)-5-Hydroxy-6-{2-(methoxycarbonylmethyl-carbamoyl)-2-[4-methoxycarbonyl-4-(2,2,2-trifluoro-acetylamino)-butyrylamino]-ethylsulfanyl}-icosa-7,9,11,14-tetraenoic acid methyl ester 
• 73957-99-0 (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 102906-05-8 (Z)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid 
• 102906-18-3 (E)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid 
• 78377-37-4 7,8-O-isopropylidene-7(R),8-dihydroxyoct-5-enoic acid 
• 82430-34-0 7,8-O-isopropylidene-7(R),8-dihydroxyoct-5-enoic acid 
• 73958-01-7 9-oxo-5,6-trans-epoxynon-7(E)-enoate 
• 78377-38-5 (E)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid methyl ester 
• 78377-38-5 (E)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hex-5-enoic acid methyl ester 
• 73958-00-6 methyl 10-formyl-5,6E-epoxy-7E,9E-decadienoate 
• 78419-54-2 4-[(2S,3R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-butyric acid methyl ester 
• 78377-39-6 4-[(2S,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-butyric acid methyl ester 

Downstream Products

• 70578-51-7 6-trans-Leukotriene B₄ 
• 70578-51-7 (5S,12S)-6-trans-leukotriene B 
• 76485-14-8 Leukotriene C4 sulfone 

Relevant academic research and scientific papers

Total synthesis of leukotrienes from butadiene

The total synthesis of leukotrienes has been achieved starting from butadiene by a palladium-catalyzed telomerization at room temperature. A Sharpless catalytic asymmetric epoxidation generated the asymmetric centers with >94% ee. Simple transformations of the key intermediate 15 produced the leukotrienes LTA4 methyl ester (4), LTC4 (1), LTD4 (2) and LTE4 (3), as well as (14S, 15S)-LTA4 methyl ester (24) and the novel [2H2]-LTA4 methyl ester (28). The use of the opposite chiral director in the Sharpless catalytic asymmetric epoxidation gave the key intermediate 15a that has been used in the synthesis of the double epimers of the leukotrienes as well as LTB4.

SYNTHESIS OF LEUKOTRIENES - NEW SYNTHESIS OF NATURAL LEUKOTRIENE A4

The acetonides of D- or L-glyceraldehyde are chiral synthons for an efficient and versatile synthesis of the natural leukotrienes A4, C4, D4 and E4 and equally can be used to prepare the corresponding unnatural analogues.

SYNTHESIS OF THE 9Z and 9Z,11E ISOMERS OF LEUKOTRIENE C4

Synthesis of the 9Z and 9Z,11E isomers of leukotriene C4 is described, the stereochemistry of the former was confirmed by its facile 1,7 hydride shift reaction.

Total synthesis of slow reacting substances (SRS). "Leukotriene C-2" (11-trans-leukotriene C) (3) and leukotriene D (4)

Syntheses are described for the "slow reacting substances" 11-trans-leukotriene C (3) (previously known as leukotriene C-2) and leukotriene D (4), the cys-gly analog of leukotriene C (2). The synthesized leukotrienes 3 and 4 were instrumental in the assignment of structure to these members of the family of naturally occuring slow reacting substances which includes also 2.

TOTAL SYNTHESIS OF SLOW REACTING SUBSTANCES (SRS's):6-EPI-LEUKOTRIENE C AND 6-EPI-LEUKOTRIENE D

6-Epi-leukotrienes C and D (3 and 4) have been synthesized unambigously via the 5(S),6(R)-epoxide (5,6-cis) wich is isomeric with leukotriene A.These 6-epi-leukotrienes are less active (especially 4) than leukotrienes C and D(1 and 2) and have not been fo