S-(5-Hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)cysteine

Base Information

• Chemical Name: S-(5-Hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)cysteine
• CAS No.: 89461-65-4
• Molecular Formula: C₂₄H₃₉NO₅S
• Molecular Weight: 453.643
• DSSTox Substance ID: DTXSID20694026
• Mol file: 89461-65-4.mol

Synonyms:89461-65-4;Leukotriene E4 methyl ester;S-(5-Hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)cysteine;DTXSID20694026;2-amino-3-(5-hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)sulfanylpropanoic acid

Chemical Property of S-(5-Hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)cysteine

Chemical Property:

• PSA: 135.15000
• LogP: 5.09980
• Storage Temp.: -20°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 19
• Exact Mass: 453.25489452
• Heavy Atom Count: 31
• Complexity: 601

Purity/Quality:

97% ^*data from raw suppliers

LeukotrieneE4methylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC=CC(C(CCCC(=O)OC)O)SCC(C(=O)O)N
• Uses: Leukotriene E4 methyl ester is a more lipid soluble form of LTE4.

Technology Process of S-(5-Hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)cysteine

There total 20 articles about S-(5-Hydroxy-1-methoxy-1-oxoicosa-7,9,11,14-tetraen-6-yl)cysteine 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:

C26H22O8 (55797-81-4,105453-39-2) → (7E,9E,11Z,14Z)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (89461-64-3,89461-65-4,89461-66-5,89461-67-6,89461-68-7,89495-44-3,92009-29-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / benzoic acid / 1,2-dimethoxy-ethane / 4 h / Heating

2: 100 percent / H₂SO₄ / 3 h / 23 °C

3: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

4: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

5: 99 percent / dry hydroden chloride / 72 h / 23 °C

6: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

7: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

8: 96 percent / Collins reagent / CH₂Cl₂ / 0.25 h / 23 °C

9: 46 percent / 1.) s-BuLi, 3.) phosphate buffer / diethyl ether / 1.) - 78 deg C, 45 min, 2.) -110 deg C, 15 min; -78 deg C, 30 min

10: 1.) hexamethylphosphoric amide / 1.) THF, -60 deg C, 10 s, 2.) -95 deg C, 20 min

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; amalgamated zinc; phosphate buffer; Collins oxidation agent; sulfuric acid; hydrogen; sec.-butyllithium; potassium carbonate; benzoic acid; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane;

DOI:10.1021/ja00524a045

Reference yield:

C32H30O10 (73957-95-6,74006-65-8) → (7E,9E,11Z,14Z)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (89461-64-3,89461-65-4,89461-66-5,89461-67-6,89461-68-7,89495-44-3,92009-29-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

2: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

3: 99 percent / dry hydroden chloride / 72 h / 23 °C

4: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

5: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

6: 96 percent / Collins reagent / CH₂Cl₂ / 0.25 h / 23 °C

7: 46 percent / 1.) s-BuLi, 3.) phosphate buffer / diethyl ether / 1.) - 78 deg C, 45 min, 2.) -110 deg C, 15 min; -78 deg C, 30 min

8: 1.) hexamethylphosphoric amide / 1.) THF, -60 deg C, 10 s, 2.) -95 deg C, 20 min

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; amalgamated zinc; phosphate buffer; Collins oxidation agent; hydrogen; sec.-butyllithium; potassium carbonate; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00524a045

Reference yield:

C30H28O9 (63753-78-6,63753-83-3) → (7E,9E,11Z,14Z)-6-(2-Amino-2-carboxy-ethylsulfanyl)-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (89461-64-3,89461-65-4,89461-66-5,89461-67-6,89461-68-7,89495-44-3,92009-29-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / H₂SO₄ / 3 h / 23 °C

2: 93 percent / 95percent zinc amalgam, dry hydrogen chloride / diethyl ether / 6 h / 15 °C

3: 100 percent / H₂ / 10percent Pd/C / methanol / 23 °C

4: 99 percent / dry hydroden chloride / 72 h / 23 °C

5: 98 percent / pyridine / 1.) 23 deg C, 6 h, 2.) 50 deg C, 3h

6: 98 percent / K₂CO₃ / methanol / 2 h / 23 °C

7: 96 percent / Collins reagent / CH₂Cl₂ / 0.25 h / 23 °C

8: 46 percent / 1.) s-BuLi, 3.) phosphate buffer / diethyl ether / 1.) - 78 deg C, 45 min, 2.) -110 deg C, 15 min; -78 deg C, 30 min

9: 1.) hexamethylphosphoric amide / 1.) THF, -60 deg C, 10 s, 2.) -95 deg C, 20 min

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; amalgamated zinc; phosphate buffer; Collins oxidation agent; sulfuric acid; hydrogen; sec.-butyllithium; potassium carbonate; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00524a045

upstream raw materials:

rac-cysteine

rac-trans-(1E,3E,5Z,8Z)-(1,3,5,8-tetradecatetraenyl)oxiranebutanoic acid methyl ester

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

(+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate

Downstream raw materials:

7Z,9E,11E,14Z-LTE₄

Refernces

• 1、 Corey,Clark,Goto,et al.. "Stereospecific total synthesis of a 'slow reacting substance' of anaphylaxis, leukotriene C-1". . p. 1436 - 1439. Retrieved 2007/10/02.