Synthesis of certain 4'-substituted nucleosides.
We have developed general methods for the synthesis of 4'-fluoro- and 4'-methoxynucleosides by addition of iodinemonofluoride or iodine and methanol across the double bond of suitably protected 4',5'-unsaturated pyrimidine and purine nucleosides. The structures of these adducts have been determined by a combination of chemical, spectroscopic, and electrophoretic methods. The 4'-methoxy- and the uridine analogs of nucleocidin have been synthesized from the corresponding 4'-fluorouridine and 4'-methoxyadenosine derivatives.
D000241:Adenosine / Q000031:analogs & derivatives; D003562:Cytidine / Q000031:analogs & derivatives; D005461:Fluorine; D007455:Iodine; D008722:Methods; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives
D009705:Nucleosides; D005461:Fluorine; D003562:Cytidine; D007455:Iodine; D000241:Adenosine; D014529:Uridine