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

Base Information

• Chemical Name: ((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(ethoxy)phosphoryl)oxy)methyl pivalate
• CAS No.: 142341-04-6
• Molecular Formula: C16H26N5O6P
• Molecular Weight: 415.38100
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90438070
• Nikkaji Number: J592.474J
• ChEMBL ID: CHEMBL54280
• Mol file: 142341-04-6.mol

Synonyms:142341-04-6;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(ethoxy)phosphoryl)oxy)methyl pivalate;9-[2-(Phosphonomethoxy)ethyl]adenine,Monoethyl Mono(pivaloyloxy)methyl Ester;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)-(ethoxy)phosphoryl)oxy)methyl pivalate;[2-(6-aminopurin-9-yl)ethoxymethyl-ethoxyphosphoryl]oxymethyl 2,2-dimethylpropanoate;PROPANOIC ACID, 2,2-DIMETHYL-, [[[[2-(6-AMINO-9H-PURIN-9-YL)ETHOXY]METHYL]ETHOXYPHOSPHINYL]OXY]METHYL ESTER;[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}(ethoxy)phosphoryl)oxy]methyl 2,2-dimethylpropanoate;{[{[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl}(ethoxy)phosphoryl]oxy}methyl 2,2-dimethylpropanoate;2,2-Dimethylpropanoic Acid [[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]ethoxyphosphinyl]oxy]methyl ester;CHEMBL54280;DTXSID90438070;NOZLVTCICOSPFI-UHFFFAOYSA-N;BCP29741;SC1443;AKOS015896452;((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(ethoxy)phosphoryl)oxy)methylpivalate;[2-(6-aminopurin-9-yl)ethoxymethyl-ethoxy-phosphoryl]oxymethyl 2,2-dimethylpropanoate;FT-0652845;A807895;[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid (pivaloyloxymethyl)=ethyl ester;2,2-dimethylpropanoic acid,((((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)ethoxyphosphinyl)oxy)methyl ester;Mono-POM Ethyl Adefovir;Mono(pivaloyloxymethyl) Ethyl Adefovir;2,2-Dimethylpropanoic acid [[[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]ethoxyphosphinyl]oxy]methyl ester

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

Chemical Property:

• Vapor Pressure: 9.87E-14mmHg at 25°C
• Melting Point: 68-70°C
• Boiling Point: 586.4oC at 760 mmHg
• Flash Point: 308.4oC
• PSA: 150.49000
• Density: 1.39g/cm3
• LogP: 2.75680
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 415.16207056
• Heavy Atom Count: 28
• Complexity: 560

Purity/Quality:

97% ^*data from raw suppliers

Mono-POM ethyl adefovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C
• Uses: An analogue of the antiviral drug Adefovir (A247500) with a mono-POM ester protecting group.

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

There total 5 articles about ((((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)(ethoxy)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: 36.99%

ethanol (64-17-5) + 9-<2-(phosphonomethoxy)ethyl>adenine, mono(pivaloyloxy)methyl ester (142341-05-7) → 9-<2-(phosphonomethoxy)ethyl>adenine, monoethyl mono(pivaloyloxy)methyl ester (142341-04-6)

Guidance literature:

9-<2-(phosphonomethoxy)ethyl>adenine, mono(pivaloyloxy)methyl ester; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 2h; Cooling with ice;

ethanol; In dichloromethane; at 20 ℃; for 3h; Cooling with ice;

Reference yield: 33.0%

Chloromethyl pivalate (18997-19-8) + 9-<2-(phosphonomethoxy)ethyl>adenine, monoethyl ester, sodium salt → 9-<2-(phosphonomethoxy)ethyl>adenine, monoethyl mono(pivaloyloxy)methyl ester (142341-04-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 22 ℃; for 48h;

DOI:10.1021/jm00038a015

Reference yield:

Adefovir (106941-25-7) → 9-<2-(phosphonomethoxy)ethyl>adenine, monoethyl mono(pivaloyloxy)methyl ester (142341-04-6)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / 1 h / Heating

2: 3 h / 60 °C

3: 52 percent / aq. NaOH / 24 h / 22 °C

4: 33 percent / Et₃N / dimethylformamide / 48 h / 22 °C

With sodium hydroxide; thionyl chloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00038a015

upstream raw materials:

Chloromethyl pivalate

Adefovir

[[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester

C₈H₁₀Cl₂N₅O₂P