2'-Deoxy-2'-alkoxyaminouridines: Novel 2'-substituted uridines prepared by intramolecular nucleophilic ring opening of 2,2'-O-anhydrouridines

Article abstract of DOI:10.1016/0040-4020(96)00870-8

Natural and unnatural modified nucleosides and nucleotides play important roles in biology, medicine, and as biomedical research tools. Reported herein is an application of synthetic methodology developed for the stereo- and regiospecific introduction of structural modifications at the 2'-position of uridine nucleosides. A novel class of modified nucleosides, 2'-alkoxylamino-2'-deoxy uridines, are prepared by intramolecular nucleophilic addition of a 3'-tethered alkoxycarbamate nucleophile to the 2'-position with concomitant opening of a 2,2'-anhydrouridine.