A SIMPLE AND GENERAL ENTRY TO 5-SUBSTITUTED URUDINES BASED ON THE REGIOSELECTIVE LITHIATHION CONTROLLED BY A PROTECTING GROUP IN THE SUGAR MOIETY

Article abstract of DOI:10.1016/S0040-4039(00)95656-9

Lithiathion of 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine with sec-BuLi/TMEDA occurs at the C-5 position with a high regioselectivity and subsequent reactions of the resulting C-5 lithiated species with a variety of electrophiles provides a general entry to 5-substituted uridines.