Collect. Czech. Chem. Commun. 2006, 71, 820-831

Nucleoside H-Phosphonates. XXI. Synthetic and 31P NMR Studies on the Preparation of Dinucleoside H-Phosphonoselenoates

Martin Kullberga, Martin Bollmarka and Jacek Stawinskib,a,*

a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden
b Institute of Bioorganic Chemistry, Polish Academy of Sciences, 61-704 Poznan, Poland


Using 31P NMR spectroscopy as a tool, we investigated the condensation of H-phosphonoselenoate monoesters with a hydroxy component in the presence of various coupling agents. On this basis, synthetic protocols that eliminate or significantly suppress side reactions which might occur during the condensation in synthesis of H-phosphonoselenoate derivatives, have been developed. Absolute configuration of the produced dinucleoside H-phosphonoselenoates has been determined by stereochemical correlation analysis.

Keywords: H-Phosphonoselenoates; H-Phosphonates; Coupling agents; 31P NMR spectroscopy; Absolute configuration assignment; Dinucleosides; Oligonucleotides.

References: 23 live references.