N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine

Base Information

• Chemical Name: N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine
• CAS No.: 1365349-72-9
• Molecular Formula: C₂₇H₄₃N₆O₇P
• Molecular Weight: 594.648
• Mol file: 1365349-72-9.mol

Synonyms:N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine

Chemical Property of N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine

There total 5 articles about N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine 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: 50.0%

N6-cyclohexyl-9H-purine-2,6-diamine (7674-43-3) + (E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate (1415634-04-6) → N9-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine (1365349-72-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 10 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2012.08.042

Reference yield: 50.0%

→ N9-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine (1365349-72-9)

Guidance literature:

Reference yield:

[({[(2,2-dimethylpropanoyl)oxy]methoxy}(prop-2-en-1-yl)phosphoryl)oxy]methyl 2,2-dimethylpropanoate (1258789-63-7) → N9-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-cyclohexylaminopurine (1365349-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1: [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(triphenylphosphine)ruthenium(II) / dichloromethane / 48 h / 40 °C / Inert atmosphere

2: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 10 - 20 °C / Inert atmosphere

With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(phenylmethylene)(triphenylphosphine)ruthenium(II); di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; dichloromethane; 2: |Mitsunobu Displacement;

DOI:10.1016/j.ejmech.2012.08.042

upstream raw materials:

N₆-cyclohexyl-9H-purine-2,6-diamine

(E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate

cyclohexylamine

2-Amino-6-chloropurin

Refernces

• 1、 Pradère, Ugo,Roy, Vincent,Montagu, Aurélien,Sari, Ozkan,Hamada, Manabu,Balzarini, Jan,Snoeck, Robert,Andrei, Graciela,Agrofoglio, Luigi A.. "Synthesis and antiviral evaluation of bis(POM) prodrugs of (E)-[4′-phosphono-but-2′-en-1′-yl]purine nucleosides". . p. 126 - 133. Retrieved 2013/01/15.