Tj. Baker et Df. Wiemer, Synthesis and rearrangement of 3 '-alpha-diethylphosphono-3 '-beta-O-methanesulfonyluridines, TETRAHEDRON, 56(20), 2000, pp. 3127-3131
Preparation of a uridine derivative bearing both diethylphosphono and metha
nesulfonate substituents at the 3'-position has been accomplished by reacti
on of the corresponding alpha-hydroxy phosphonate with methanesulfinyl chlo
ride and subsequent oxidation. While this methanesulfonate did not undergo
elimination under standard reaction conditions, treatment with TBAF results
in a novel rearrangement leading to the corresponding 2'-phosphate. (C) 20
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