116384-54-4

Basic information

• Product Name: Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-, monoethyl ester
• Synonyms: Phosphonic acid,[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-,monoethyl ester;[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid monoethyl ester
• CAS NO: 116384-54-4
• Molecular Formula: C10H16N5O4P
• Molecular Weight: 301.23900
• Mol File: 116384-54-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 552.3±60.0 °C(Predicted)
• Density: 1.62±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-, monoethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-, monoethyl ester(116384-54-4)
• EPA Substance Registry System: Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-, monoethyl ester(116384-54-4)

Safety Data

• Hazardous Substances Data: 116384-54-4(Hazardous Substances Data)

Usage

Uses

O-Ethyl Adefovir is an intermediate in the synthesis of Mono-POM Ethyl Adefovir (M567050), which is an analogue of the antiviral drug Adefovir (A247500) with a mono-POM ester protecting group.

Upstream product

• 64-17-5 ethanol 
• 106941-25-7 Adefovir 
• 116384-58-8 toluene-4-sulfonic acid 2-(diethoxy-phosphorylmethoxy)-ethylester 
• 116384-57-7 Diethyl 2-Bromoethoxymethanephosphonate 
• 116384-55-5 diethyl 2-hydroxyethoxymethanephosphonate 
• 116384-56-6 2-chloroethoxymethyl phosphonic acid diethyl ester 
• 100708-15-4 2-((diethoxyphosphoryl)methoxy)ethyl acetate 
• 116384-53-3 [[2-(6-amino-9H-purine-9-yl)ethoxy]methyl]phosphonic acid diethyl ester 

Relevant articles and documents

Method to improve antiviral activity of nucleotide analogue drugs

An amino acid conjugate of a cyclic or acyclic nucleoside phosphonate is provided. In some cases, the amino acid conjugate is a tyrosine alkyl amide phosphonate ester conjugate of a cyclic or acyclic nucleoside phosphonate, and is useful as an antiviral c

SYNTHESIS OF 9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE AND RELATED COMPOUNDS

Diethyl 2-hydroxyethoxymethanephosphonate (VIII) was converted into diethyl 2-halogenoethoxymethanephosphonates IXa and IXb by reaction with triphenylphosphine and tetrachloromethane or tetrabromomethane; analogous reaction of VIII with p-toluenesulfonyl chloride afforded diethyl 2-(p-toluenesulfonyloxy)ethoxymethanephosphonate (IXc).Reaction of sodium salt of adenine with compounds IX led to 9-(2-diethoxyphosphonylmethoxyethyl)adenine (X).Compound X was converted into 9-(2-phosphonylmethoxyethyl)adenine (II) by treatment with bromotrimethylsilane whereas alkaline hydrolysis of X gave ethyl ester Vb.Reaction of 9-(2-hydroxyethyl)adenine (IIIa) or its N6-benzoyl derivative IIIb with dimethyl p-toluenesulfonyloxymethanephosphonate (IV) in the presence of sodium hydride, followed by alkaline hydrolysis yielded methyl ester Va.Morpholide XI reacted with an inorganic phosphate and diphosphate to give 9-(2-phosphorylphosphonylmethoxyethyl)adenine (XII) and 2-(diphosphorylphosphonylmethoxyethyl)adenine (XIII), respectively.