{[2-(2-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid

Base Information

• Chemical Name: {[2-(2-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid
• CAS No.: 113852-42-9
• Molecular Formula: C8H12 N5 O4 P
• Molecular Weight: 273.188
• Mol file: 113852-42-9.mol

Synonyms:Phosphonicacid, [[2-(2-amino-9H-purin-9-yl)ethoxy]methyl]- (9CI);2-Amino-9-[2-(phosphonomethoxy)ethyl]purine

Chemical Property of {[2-(2-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid

Chemical Property:

• Vapor Pressure: 1.31E-18mmHg at 25°C
• Boiling Point: 665.3°Cat760mmHg
• Flash Point: 356.2°C
• Density: 1.88g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of {[2-(2-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid

There total 3 articles about {[2-(2-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic 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: 95.0%

[2-(2-amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester (228874-36-0) → 6-amino-9-[2-(phosphonomethoxy)ethyl]-9H-purine (113852-42-9)

Guidance literature:

[2-(2-amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester; With trimethylsilyl bromide; In acetonitrile; at 0 - 20 ℃;

In DMF (N,N-dimethyl-formamide); acetonitrile; for 2h;

In methanol; DMF (N,N-dimethyl-formamide); acetonitrile; for 2h;

Reference yield:

[[2-(2-amino-6-chloro-9H-purin-9-yl)ethoxy]methyl]phosphonic acid bis(1-methylethyl)ester (183194-25-4) → 6-amino-9-[2-(phosphonomethoxy)ethyl]-9H-purine (113852-42-9)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, aq. HCl / 10 percent Pd/C / methanol / Ambient temperature

2: acetonitrile / Ambient temperature

3: aq. NH₃

With hydrogenchloride; ammonium hydroxide; hydrogen; palladium on activated charcoal; In methanol; acetonitrile;

DOI:10.1021/jm9811256

Reference yield:

C14H28N5O4PSi2 → 6-amino-9-[2-(phosphonomethoxy)ethyl]-9H-purine (113852-42-9)

Guidance literature:

With ammonium hydroxide; Yield given;

DOI:10.1021/jm9811256

upstream raw materials:

[[2-(2-amino-6-chloro-9H-purin-9-yl)ethoxy]methyl]phosphonic acid bis(1-methylethyl)ester

[2-(2-amino-purin-9-yl)-ethoxymethyl]-phosphonic acid diisopropyl ester

Downstream raw materials:

C₂₅H₂₉N₆O₅P

Refernces

• 1、 Holy, Antonín,Günter, Jaroslav,Dvo?áková, Hana,Masojídková, Milena,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,De Clercq, Erik. "Structure-antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy)ethyl] nucleotide analogues. 1. Derivatives substituted at the carbon atoms of the base". . p. 2064 - 2086. Retrieved 2007/10/03.