A new approach for the synthesis of novel 5-substituted isodeoxyuridine analogs.
Cyclic sulfates of carbohydrates provide excellent synthons for the preparation of isodeoxyuridines through direct nucleophilic substitution reactions. These substitution reactions have exceptional regioselectivity. The products of the reactions served as key precursors for the synthesis of 5-substituted isodeoxyuridines via the Stille and Heck coupling reactions. Interestingly, unprotected nucleosides could be used in these metal-mediated functionalizations. The methodologies are general and allow ready access to a variety of C-5 functionalized isomeric deoxyuridines, but also have the potential to be extended to other nucleoside analogs.
Guenther
Sven
S
Department of Pharmaceutical and Biomedical Sciences, University of Georgia, Athens, Georgia 30602, USA.
Nair
Vasu
V
D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy
D003857:Deoxyuridine