Tetrahedron p. 14385 - 14402 (1996)
Update date:2022-09-26
Topics:
Sebesta, David P.
O'Rourke, Sarah S.
Martinez, Rogelio L.
Pieken, Wolfgang A.
McGee, Danny P. C.
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.
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