2'-DEOXY-2'-ALKOXYLAMINOURIDINES - NOVEL 2'-SUBSTITUTED URIDINES PREPARED BY INTRAMOLECULAR NUCLEOPHILIC RING-OPENING OF 2,2'-O-ANHYDROURIDINES

Natural and unnatural modified nucleosides and nucleotides play import ant roles in biology, medicine, and as biomedical research tools. Repo rted herein is an application of synthetic methodology developed for t he stereo- and regiospecific introduction of structural modifications at the 2'-position of uridine nucleosides. A novel class of modified n ucleosides, 2'-alkoxylamino-2'-deoxy uridines, are prepared by intramo lecular nucleophilic addition of a 3'-tethered alkoxycarbamate nucleop hile to the 2'-position with concomitant opening of a 2,2'-anhydrourid ine. Copyright (C) 1996 Elsevier Science Ltd