Synthesis of ether-linked oligoribo- and xylonucleosides from 3,5'-ether-linked pseudosaccharides

First examples of di- and trinucleosides with ribose and xylose stereochemistry having internucleoside ether linkage were synthesized from 3,5'-ether-linked pseudosaccharides. The synthetic protocol involved removal of 1,2-isopropylidene protecting groups from the pseudosaccharides followed by acetylation and a subsequent Vorbruggen transglycosylation with uracil and N-benzoylaminopurine. The synthetic strategy is potentially important for the development of RNA analogues with internucleoside ether linkage.