Carbocyclic thromboxane A2

Base Information

• Chemical Name: Carbocyclic thromboxane A2
• CAS No.: 74034-56-3
• Molecular Formula: C₂₂H₃₆O₃
• Molecular Weight: 348.526
• UNII: 0K593AJ3OL
• Nikkaji Number: J261.830C
• Wikidata: Q27075708
• Pharos Ligand ID: WHVYDUWXZ8LV
• Mol file: 74034-56-3.mol

Synonyms:2 beta-(Z),3 alpha-(1E,3R)-3-(3-hydroxy-(1-octenyl)bicyclo(3.1.1)hept-2-yl)-5-heptenoic acid;carbocyclic thromboxane A2;thromboxane A2, carbocyclic

Chemical Property of Carbocyclic thromboxane A2

Chemical Property:

• PSA: 57.53000
• LogP: 5.34730
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 348.26644501
• Heavy Atom Count: 25
• Complexity: 448

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

CarbocyclicThromboxaneA2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1CC2CC(C2)C1CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1CC2CC(C2)[C@@H]1C/C=C\CCCC(=O)O)O
• Description: Carbocyclic thromboxane A2 (CTA2) is a stable analog of TXA2. CTA2 is a potent coronary vasoconstrictor and is effective at concentrations as low as 1 nM in cat coronary arteries. Unlike other vascular TP receptor agonists, CTA2 is a potent inhibitor of prostanoid-induced platelet aggregation. It inhibits arachidonic acid-induced aggregation with an IC50 value of 4-5 μM. CTA2 also exhibits selective and dose-dependent inhibition of TXB2 synthesis in rabbit platelets at concentrations between 1 and 100 μM.
• Uses: Carbocyclic Thromboxane A2 is a stable analog of TXA2 which inhibits thromboxane-mediated vasoconstriction platelet aggregation. Also, it converts the thromboxane synthase (TXAS) heme cofactor to its 5-coordinate.

Technology Process of Carbocyclic thromboxane A2

There total 28 articles about Carbocyclic thromboxane A2 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: 88.0%

methyl (2R*,3S*)-(Z)-((E)-3-hydroxy-1-octenyl)bicyclo<3.1.1>heptane-2-hept-5-enoate (73509-45-2,73543-46-1,73837-11-3,74034-54-1,74034-55-2,84171-72-2) → (+/-)-dimethanothromboxane A2 (73509-46-3,73543-47-2,73804-44-1,74034-56-3,74034-57-4,84171-73-3)

Guidance literature:

With potassium hydroxide; In ethanol; at 45 ℃; for 0.833333h;

DOI:10.1016/S0040-4020(01)88648-8

Reference yield:

(Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid methyl ester (73509-45-2,73543-46-1,73837-11-3,74034-54-1,74034-55-2,84171-72-2) → (Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid (73509-46-3,73543-47-2,73804-44-1,74034-56-3,74034-57-4,84171-73-3)

Guidance literature:

With potassium hydroxide; In ethanol; at 45 ℃; for 0.833333h;

DOI:10.1016/S0040-4020(01)88648-8

Reference yield:

1-tributylphosphoranylidene-2-heptanone (35563-52-1) → (Z)-7-[(2S,3R)-3-((E)-(R)-3-Hydroxy-oct-1-enyl)-bicyclo[3.1.1]hept-2-yl]-hept-5-enoic acid (73509-46-3,73543-47-2,73804-44-1,74034-56-3,74034-57-4,84171-73-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / diethyl ether / 24 h

2: 88 percent / NaBH₄ / methanol / 0.83 h / -40 °C

3: 94 percent / p-TsOH / CH₂Cl₂ / 0.33 h / 0 °C

4: DIBAL / toluene / 0.33 h / -50 °C

5: Et₃N, SO₃-pyridine / dimethylsulfoxide / 20 h

6: 1.) dimsylsodium / 1.) DMSO, 30 deg C, 1 h, 40 deg C, 1 h, 2.) ether

7: 32 percent / PPTS / methanol / 2 h / 55 °C

8: 5percent KOH / ethanol / 0.83 h / 45 °C

With potassium hydroxide; sodium tetrahydroborate; pyridine-SO₃ complex; dimsylsodium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4020(01)88648-8

upstream raw materials:

2-(6-carbomethoxyhex-(2Z)-enyl)-3β-(3α-hydroxyoct-(1E)-enyl)bicyclo<3.1.1>heptane

(4-carboxybutyl)triphenylphosphonium bromide

(4-carboxybutylene)triphenylphosphorane

(Z)-7-{(2S,3R)-3-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-bicyclo[3.1.1]hept-2-yl}-hept-5-enoic acid

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