U-75302

Base Information

• Chemical Name: U-75302
• CAS No.: 119477-85-9
• Molecular Formula: C₂₂H₃₅NO₃
• Molecular Weight: 361.525
• European Community (EC) Number: 634-249-7
• ChEMBL ID: CHEMBL110037
• Mol file: 119477-85-9.mol

Synonyms:6-(6-(3-hydroxy-1,5-undecadien-1-yl)-2-pyridinyl)-1,5-hexanediol;U 75302;U-75302;U75302

Chemical Property of U-75302

Chemical Property:

• Appearance/Colour: light yellow oil
• Vapor Pressure: 1.05E-13mmHg at 25°C
• Boiling Point: 567.2 °C at 760 mmHg
• Flash Point: 296.8 °C
• PSA: 73.58000
• Density: 1.058 g/cm³
• LogP: 4.04830
• Storage Temp.: −20°C
• Solubility.: DMSO: 10 mg/mL
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 361.26169398
• Heavy Atom Count: 26
• Complexity: 384

Purity/Quality:

99% ^*data from raw suppliers

U-75302 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(C=CC1=CC=CC(=N1)CC(CCCCO)O)O
• Isomeric SMILES: CCCCC/C=C\CC(/C=C/C1=CC=CC(=N1)CC(CCCCO)O)O
• Description: U-75302 is an LTB4 receptor antagonist with a Ki of 159 nM on guinea pig lung membranes. This activity is specific for the BLT1 receptor; U-75302 does not antagonize the binding of [3H]-LTB4 to the human BLT2 receptor.
• Uses: U-75302 is a selective leukotriene B4 antagonist.

Technology Process of U-75302

There total 15 articles about U-75302 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: 92.0%

6-[6-((Z)-3-Hydroxy-undec-5-en-1-ynyl)-pyridin-2-ylmethyl]-tetrahydro-pyran-2-one (116897-21-3,117160-70-0,118824-73-0) → U-75302 (116897-14-4,116897-22-4,118789-86-9,119477-85-9,127760-28-5,127760-29-6,127760-30-9)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 23 ℃;

DOI:10.1016/S0040-4039(00)80037-4

Reference yield: 83.0%

(S)-6-[6-((Z)-(R)-3-Hydroxy-undec-5-en-1-ynyl)-pyridin-2-yl]-hexane-1,5-diol (127705-36-6) → U 75302 (119477-85-9)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride;

DOI:10.1016/S0040-4039(01)93452-5

Reference yield:

6-bromo-2-pyridinecarbaldehyde (34160-40-2) → U-75302 (116897-14-4,116897-22-4,118789-86-9,119477-85-9,127760-28-5,127760-29-6,127760-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1: LiN(TMS)2 / tetrahydrofuran / Ambient temperature

2: 71 percent / n-Bu₃SnH / AIBN / toluene / 75 °C

3: 99 percent / acetylene, (bis)triphenyl-phosphinepalladium-dichloride / Pd-Cu / triethylamine / 4 h / 50 °C

4: 92 percent / sodium (bis)-2-methoxyethoxy aluminium hydride (Red-Al) / toluene / 23 °C

With bis-triphenylphosphine-palladium(II) chloride; tri-n-butyl-tin hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; acetylene; 2,2'-azobis(isobutyronitrile); copper; palladium; In tetrahydrofuran; triethylamine; toluene;

DOI:10.1016/S0040-4039(00)80037-4

upstream raw materials:

6-[6-((Z)-3-Hydroxy-undec-5-en-1-ynyl)-pyridin-2-ylmethyl]-tetrahydro-pyran-2-one

6-bromo-2-pyridinecarbaldehyde

(4-carboxybutyl)triphenylphosphonium bromide

6-(6-Bromopyridine-2-yl)methyl-tetrahydropyran-2one

Refernces

• 1、 Morris, Joel,Wishka, Donn G.. "SYNTHESIS OF NOVEL ANTAGONISTS OF LEUKOTRIENE B4". . p. 143 - 146. Retrieved 2007/10/02.