((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methyl pivalate

Base Information

• Chemical Name: ((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methyl pivalate
• CAS No.: 142341-05-7
• Molecular Formula: C₁₄H₂₂N₅O₆P
• Molecular Weight: 387.332
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70438750
• Nikkaji Number: J592.471E
• Wikidata: Q72436725
• ChEMBL ID: CHEMBL54393
• Mol file: 142341-05-7.mol

Synonyms:142341-05-7;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methyl pivalate;Adefovir Monopivoxil;2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphinic Acid;Propanoic acid, 2,2-dimethyl-, [[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]hydroxyphosphinyl]oxy]methyl ester;9-[2-(Phosphonomethoxy)ethyl]adenine,Mono(pivaloyloxy)methyl Ester;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)-(hydroxy)phosphoryl)oxy)methyl pivalate;Mono POM PMEA;CHEMBL54393;SCHEMBL12391569;DTXSID70438750;BCP20815;SC1440;AKOS015896453;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methylpivalate;2,2-Dimethylpropanoic Acid [[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]hydroxyphosphinyl]oxy]methyl Ester;FT-0654975;A807896;J-007641;9-[2-[[(Pivaloyloxymethyl)phosphono]methoxy]ethyl]-9H-purin-6-amine;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)hydroxyphosphinyl)oxy)methyl 2,2-dimethylpropanoate;{[{[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl}(hydroxy)phosphoryl]oxy}methyl 2,2-dimethylpropanoate;{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphinic acid;2,2-dimethylpropanoic acid,((((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)hydroxyphosphinyl)oxy)methyl ester

Chemical Property of ((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methyl pivalate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >137°C (dec.)
• Boiling Point: 597.669oC at 760 mmHg
• Flash Point: 315.259oC
• PSA: 161.49000
• Density: 1.506g/cm3
• LogP: 1.71260
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 387.13077044
• Heavy Atom Count: 26
• Complexity: 530

Purity/Quality:

97% ^*data from raw suppliers

Adefovir Monopivoxil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)O
• Uses: The monoester metabolite of the adefovir prodrug Adefovir Dipivoxil (A280465).

Technology Process of ((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methyl pivalate

There total 6 articles about ((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(hydroxy)phosphoryl)oxy)methyl pivalate 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:

2,2-Dimethyl-propionic acid [2-(6-amino-purin-9-yl)-ethoxymethyl]-benzyloxy-phosphinoyloxymethyl ester (158421-65-9) → 9-<2-(phosphonomethoxy)ethyl>adenine, mono(pivaloyloxy)methyl ester (142341-05-7)

Guidance literature:

With water; hydrogen; cyclohexene; palladium dihydroxide; In ethanol; for 1h; Yield given;

DOI:10.1021/jm00038a015

Reference yield:

Chloromethyl pivalate (18997-19-8) → 9-<2-(phosphonomethoxy)ethyl>adenine, mono(pivaloyloxy)methyl ester (142341-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / dimethylformamide / 2 h / 22 °C

2: H₂, H₂O, cyclohexene / 20percent Pd(OH)2/C / ethanol / 1 h

With water; hydrogen; triethylamine; cyclohexene; palladium dihydroxide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00038a015

Reference yield:

Adefovir (106941-25-7) → 9-<2-(phosphonomethoxy)ethyl>adenine, mono(pivaloyloxy)methyl ester (142341-05-7)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride / 1 h / Heating

2: acetonitrile / 20 h / 22 °C

3: 68 percent / sodium hydride / dimethylsulfoxide / 1 h / 22 °C

4: Et₃N / dimethylformamide / 2 h / 22 °C

5: H₂, H₂O, cyclohexene / 20percent Pd(OH)2/C / ethanol / 1 h

With thionyl chloride; water; hydrogen; sodium hydride; triethylamine; cyclohexene; palladium dihydroxide; In ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00038a015

upstream raw materials:

2,2-Dimethyl-propionic acid [2-(6-amino-purin-9-yl)-ethoxymethyl]-benzyloxy-phosphinoyloxymethyl ester

Chloromethyl pivalate

Adefovir

C₈H₁₀Cl₂N₅O₂P