(5S,6R,7E,9E,11Z,14Z)-6-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid

Base Information

• Chemical Name: (5S,6R,7E,9E,11Z,14Z)-6-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid
• CAS No.: 73836-78-9
• Molecular Formula: C25H40N2O6S
• Molecular Weight: 496.66
• ChEMBL ID: CHEMBL1521056
• DSSTox Substance ID: DTXSID6040533
• Pharos Ligand ID: 4YCA9C5VUHLW
• Wikidata: Q27082010
• Mol file: 73836-78-9.mol

Synonyms:Leukotriene D;Leukotriene D 4;Leukotriene D-4;Leukotriene D4;Leukotrienes D;LTD4

Chemical Property of (5S,6R,7E,9E,11Z,14Z)-6-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid

Chemical Property:

• Vapor Pressure: 1.57E-28mmHg at 25°C
• Refractive Index: 1.558
• Boiling Point: 785.8 °C at 760 mmHg
• PKA: 3.03±0.10(Predicted)
• Flash Point: 429 °C
• PSA: 175.25000
• Density: 1.162 g/cm³
• LogP: 4.51850
• Storage Temp.: −70°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 20
• Exact Mass: 496.26070817
• Heavy Atom Count: 34
• Complexity: 706

Purity/Quality:

97% ^*data from raw suppliers

LTD4(LeukotrieneD4) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CC=CC=CC(C(CCCC(=O)O)O)SCC(C(=O)NCC(=O)O)N
• Isomeric SMILES: CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SCC(C(=O)NCC(=O)O)N
• Description: Leukotriene D4 (LTD4) is an active metabolite of LTC4 (Item Nos. 20210 | 10007241) and a constituent of slow-reacting substance of anaphylaxis (SRS-A). It is formed via metabolism of LTC4 by γ-glutamyl transpeptidase. Like LTC4, LTD4 (0.01-0.1 pM) induces contractions in isolated guinea pig parenchymal strips and tracheal spirals. In vivo, LTD4 increases insufflation pressure, a marker of bronchoconstriction, in anesthetized guinea pigs by 100% when administered at a dose of 89 pmol per animal. It also increases vascular permeability in guinea pig skin when administered intradermally at a dose of 0.1 pmol per animal.
• Uses: LTD4 (Leukotriene D4) is a member of the leukotriene family shown to be a potent contractor of smooth muscle.

Technology Process of (5S,6R,7E,9E,11Z,14Z)-6-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid

There total 38 articles about (5S,6R,7E,9E,11Z,14Z)-6-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid 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: 90.0%

Dimethyl ester of N-trifluoroacetyl leukotriene D (76322-44-6,80559-09-7,80656-98-0,80656-99-1,80657-00-7,80657-01-8,80657-02-9,80657-03-0,82467-20-7,83377-29-1,83861-12-5,83861-13-6) → Leukotriene D (73836-78-9,76738-46-0,79768-40-4,80183-71-7,80183-73-9,81026-43-9,81026-44-0,81026-45-1,81026-46-2,81026-47-3,81027-48-7,82263-72-7,82468-18-6,84823-18-7)

Guidance literature:

With potassium carbonate; In methanol; water; at 23 ℃; for 18h;

DOI:10.1016/S0040-4039(00)77430-2

Reference yield: 82.0%

N-trifluoroacetyl-leukotriene D4 dimethyl ester (76322-44-6) → leukotriene D4 (73836-78-9)

Guidance literature:

With potassium carbonate; In methanol; water; at 0 ℃; for 3.5h;

DOI:10.1002/1099-0690(200009)2000:17<2991::AID-EJOC2991>3.0.CO;2-H

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → (7E,9E,11Z,14Z)-(5R,6S)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid (73836-78-9,76738-46-0,79768-40-4,80183-71-7,80183-73-9,81026-43-9,81026-44-0,81026-45-1,81026-46-2,81026-47-3,81027-48-7,82263-72-7,82468-18-6,84823-18-7)

Guidance literature:

Multi-step reaction with 10 steps

1: dimsyl sodium

2: PhSSPh / cyclohexane / 4 h / Irradiation

4: m-CPBA / CH₂Cl₂

5: NaIO₄, H₂O / acetic acid

6: 84 percent / benzene / Heating

7: 34 percent / benzene / Heating

8: 56 percent

9: (C₂H₅)3N / methanol

10: K₂CO₃ / methanol; H₂O

With sodium periodate; water; sodium methylsulfinylmethanide; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; diphenyldisulfane; In methanol; dichloromethane; cyclohexane; water; acetic acid; benzene;

DOI:10.1016/S0040-4039(01)82844-6

upstream raw materials:

N-(N-trifluoroacetylcysteinyl)-glycine methyl ester

5S,6R-6-epi-Leukotriene A₄ methyl ester

methyl 5-(S),6-(S)-oxido-7-oxoheptanoate

methyl 10-formyl-5(S),6(S)-oxido-7(E),9(E)-decadienoate

Downstream raw materials:

N-acetyl-leukotriene D

Leukotriene D4 sulfone

Refernces

CONFORMATIONALLY RESTRICTED LEUKOTRIENE ANTAGONISTS. STEREOSELECTIVE SYNTHESIS OF SOME LEUKOTRIENE D₄ ANALOGS

10.1016/S0040-4020(01)86751-X

This research describes the stereocontrolled synthesis of conformationally restricted LTD4 (leukotriene D4) analogs 2a and 2b, which are potential LTD4 receptor antagonists for treating asthma and other hypersensitivity responses. The synthesis process involves several steps: first, the epoxidation of enone 4 yields a mixture of trans-epoxide 5 and cis-epoxide 9. Then, stereoselective Wittig olefination of these epoxides leads to Z-olefins 6 and 10, respectively. Next, regiospecific epoxide ring opening with methyl mercaptoacetate forms diesters 8 and 12, which are subsequently converted to the final products, lactones 2a and 2b, through saponification. The study also includes detailed experimental procedures and characterizations of the synthesized compounds. The results show that 2a is a competitive antagonist of LTD4 and LTE4 with a pA2 value of 6.7, and it can effectively inhibit LTD4-induced increases in lung inflation pressure in vivo at doses of 10-30 mg/kg. Isomer 2b exhibits a similar in vitro profile but is slightly less potent.