7Z,9E,11E,14Z-LTD₄ methyl ester

Base Information

• Chemical Name: 7Z,9E,11E,14Z-LTD₄ methyl ester
• CAS No.: 91944-21-7
• Molecular Formula: C₂₆H₄₂N₂O₆S
• Molecular Weight: 510.695
• Mol file: 91944-21-7.mol

Synonyms:

Chemical Property of 7Z,9E,11E,14Z-LTD₄ methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7Z,9E,11E,14Z-LTD₄ methyl ester

There total 20 articles about 7Z,9E,11E,14Z-LTD₄ 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:

C26H22O8 (55797-81-4,105453-39-2) → (7E,9E,11Z,14Z)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (91944-21-7,103476-23-9)

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-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (91944-21-7,103476-23-9)

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-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (91944-21-7,103476-23-9)

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:

cysteinyl glycine

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-LTD₄

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.