Geminal hydroxy phosphonate derivatives of nucleosides: A novel class of nucleoside 5′-monophosphate analogues

A novel type of phosphonate-based, isopolar, nonisosteric 5′-nucleotide analogue, the nucleoside 5′-hydroxy phosphonates, was prepared by Abramov nucleophilic addition of various phosphorous acid esters to nucleoside 5′-aldehydes. The newly formed compounds are distinguished by chirality of the 5′-carbon atom. The configuration of the 5′-epimers was assigned from NMR spectra.