183505-84-2Relevant academic research and scientific papers
Electrophile-promoted addition of hydroxymethylphosphonate to 4′,5′-didehydronucleosides: a way to novel isosteric analogues of 5′-nucleotides
To?ík, Zdeněk,Dvo?áková, Ivana,Liboska, Radek,Budě?ínsky, Milo?,Masojídková, Milena,Rosenberg, Ivan
, p. 4516 - 4534 (2008/02/01)
An electrophile-promoted addition of dialkyl-hydroxymethylphosphonate to the protected 4′,5′-didehydronucleosides resulted in an epimeric mixture of 4′-dialkylphosphonomethoxy derivatives of 2′,5′-dideoxynucleosides, novel analogues of 2′-deoxynucleoside 5′-monophosphates. Several types of electrophiles (pyridinium tosylate, NIS, NBS, MCPBA and others) were evaluated in addition reactions with 4′,5′-didehydrothymidine. Out of them, pyridinium tosylate was found to have a practical usefulness in these transformations. Its use has led to the preparation of a series of 4′-phosphonomethoxy derivatives of common 2′-deoxynucleosides. On biological screening, these free phosphonic acids exerted no significant cytostatic or antiviral activity.
Preparation of 4'-Phosphonomethoxy Derivatives of Nucleosides: Addition of Hydroxymethanephosphonic Acid Dialkyl Esters to 4',5'-Didehydronucleosides
Tocik, Zdenek,Kavenova, Iva,Rosenberg, Ivan
, p. S76 - S80 (2007/10/03)
A synthetic route to the preparation of 4'-phosphonomethoxy derivatives of nucleosides, structural analogs to a number of important antivirals, has been elaborated.Principle of the method consists in the reaction of suitable electrophile with 4',5'-didehydronucleoside, compound with a vinylether-type exocyclic double bond, followed by nucleophilic attack of hydroxymethanephosphonic acid dialkyl ester.Obtained products are structurally related to nucleoside 5'-monophosphates branched in 4'-position.Their use as part of building blocks for oligonucleotide synthesis is also envisaged.
