76738-48-2

Basic information

• Product Name: 4-[(2S,3R)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester
• CAS NO: 76738-48-2
• Molecular Weight: 224.257
• Mol File: 76738-48-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-[(2S,3R)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(2S,3R)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester(76738-48-2)
• EPA Substance Registry System: 4-[(2S,3R)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester(76738-48-2)

Safety Data

• Hazardous Substances Data: 76738-48-2(Hazardous Substances Data)

Upstream product

• 82393-39-3 (2E)-4-triphenylphosphoranylidene-2-butenal 
• 73427-12-0 (+)-(S,R-trans)-3-formyloxiranebutanoic acid methyl ester 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 73427-12-0 4-((2S,3S)-3-Formyl-oxiranyl)-butyric acid methyl ester 
• 73958-01-7 9-oxo-5,6-trans-epoxynon-7(E)-enoate 
• 78377-39-6 4-[(2S,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oxiranyl]-butyric acid methyl ester 
• 107751-36-0 (S)-6-[(S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-tetrahydro-pyran-2-one 
• 78377-37-4 7,8-O-isopropylidene-7(R),8-dihydroxyoct-5-enoic acid 
• 107751-37-1 3-Formylallyl(triphenyl)arsonium bromide 
• 73427-12-0 methyl 6-formyl-5,6-trans-epoxyhexanoate 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 63753-78-6 C₃₀H₂₈O₉ 
• 73957-96-7 C₂₅H₂₆O₈ 
• 73957-98-9 C₂₉H₃₀O₉S 

Downstream Products

• 73466-12-3 Leukotriene A₄ methyl ester 
• 75715-89-8 leukotriene E4 
• 73836-78-9 leukotriene D4 
• 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 
• 73958-10-8 Leukotriene C₄ methyl ester 
• 75443-89-9 (7E,9E,11Z,14Z)-(5R,6S)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 73836-78-9 (7E,9E,11Z,14Z)-(5R,6S)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid 
• 72025-60-6 leukotriene C1 
• 73836-78-9 7Z,9E,11E,14Z-LTD₄ 
• 91944-21-7 7Z,9E,11E,14Z-LTD₄ methyl ester 
• 89461-64-3 7Z,9E,11E,14Z-LTE₄ methyl ester 
• 75443-89-9 7Z,9E,11E,14Z-LTE₄ 
• 72297-14-4 4-[(2S,3R)-((1Z,3E,5E,8Z)-3-Tetradeca-1,3,5,8-tetraenyl)-oxiranyl]-butyric acid methyl ester 
• 109707-62-2 (+/-)-16-oxa-14,15-dinor-13,16-inter-o-phenyleneleucotriene A₄ methyl ester 

Relevant articles and documents

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 leukotriene analogs

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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.