RESUMO
A new method for the synthesis of 2'-O-aryluridines was developed via the microwave-mediated reaction of 2,2'-anhydrouridine with aromatic alcohols. Aminophenol and aminonaphthol derivatives underwent selective 2'-O-arylation with 2,2'-anhydrouridine to produce 2'-O-(aminoaryl)uridine derivatives. These reactions proved to proceed without the need for any bases or solvents, but better results were obtained by use of N,N-dimethylacetamide (DMA) as the solvent in some cases.
Assuntos
Micro-Ondas , Uridina/análogos & derivados , Uridina/síntese química , Álcoois/química , Catálise , Técnicas de Química Combinatória , Estrutura Molecular , Uridina/químicaRESUMO
A new method for the synthesis of natural RNAs was developed via 2'-O-cyanoethylated RNA derivatives as available precursors. It was found that the cyanoethyl groups of 2'-O-cyanoethylated RNAs could be removed by use of the reverse reaction of the Michael addition of alcohols with acrylonitrile to afford 2'-unprotected RNAs. In addition, new ribonucleoside 3'-phosphoramidite building blocks having the cyanoethyl group as the 2'-hydroxyl protecting group have sterically less hindered circumstance around the 3' reaction site than the commercially available phosphoramidite building blocks.