Reductive-desulfonylation of 2'-deoxy-2'-fluoro-2'-arylsulfonyluridine analogues (e.g. 1  , 2' R/S ~ 1:4.5, Ar = 4-MeOC6H4; J. Org. Chem. 1992 , 57, 2357) with organic electron donors such as tetrakis(dimethylamino)ethylene (TDAE) produced a mixture of the protected 2',3'-dideoxy-2',3'-didehydro-2'-fluorouridine 2  and epimeric mixture of 2'-deoxy-2'-fluoro derivatives 3  in 50% combined yield. Cyclic voltammetry experiments and effect of different electron donors, temperature, protecting groups, and solvents will be discussed. 

Reductive desulfonylation of 2'-(arylsulfonyl)-2'-deoxy-2'-fluorouridine derivatives with tetrakis(dimethylamino)ethylene

245th National Meeting (2013)

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