LEUKOTRIENE C4 METHYL ESTER

Base Information

• Chemical Name: LEUKOTRIENE C4 METHYL ESTER
• CAS No.: 73958-10-8
• Molecular Formula: C31H49N3O9S
• Molecular Weight: 639.8005
• Mol file: 73958-10-8.mol

Synonyms:N-Methyl ltc4;Ltc4 ME;Leukotriene C methyl ester;Leukotriene C4 monomethyl ester;

Chemical Property of LEUKOTRIENE C4 METHYL ESTER

Chemical Property:

• Vapor Pressure: 1.81E-33mmHg at 25°C
• Boiling Point: 848.3°C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 466.8°C
• PSA: 230.65000
• Density: 1.208g/cm³
• LogP: 4.34740
• Storage Temp.: -20°C

Purity/Quality:

97% ^*data from raw suppliers

Leukotriene C4 methyl ester ≥97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 10
• Safety Statements: 7-16-23-45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Leukotriene C4 methyl ester is a more lipid-soluble form of LTC4.

Technology Process of LEUKOTRIENE C4 METHYL ESTER

There total 29 articles about LEUKOTRIENE C4 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)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (73958-10-8,74841-70-6,84823-29-0,84823-30-3,89461-60-9,89461-61-0,89461-62-1,89461-63-2,92009-28-4,113830-70-9,113830-71-0,113830-72-1)

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

11: Et₃N / methanol / 4 h / 23 °C

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; triethylamine; 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)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (73958-10-8,74841-70-6,84823-29-0,84823-30-3,89461-60-9,89461-61-0,89461-62-1,89461-63-2,92009-28-4,113830-70-9,113830-71-0,113830-72-1)

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

9: Et₃N / methanol / 4 h / 23 °C

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; amalgamated zinc; phosphate buffer; Collins oxidation agent; hydrogen; sec.-butyllithium; potassium carbonate; triethylamine; 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)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester (73958-10-8,74841-70-6,84823-29-0,84823-30-3,89461-60-9,89461-61-0,89461-62-1,89461-63-2,92009-28-4,113830-70-9,113830-71-0,113830-72-1)

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

10: Et₃N / methanol / 4 h / 23 °C

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; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00524a045

upstream raw materials:

glutathion

5,6-oxido-7,9,11,14-eicosa-pentaenoate

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

Leukotriene A₄ methyl ester

Downstream raw materials:

(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

leukotriene C1

(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

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.