Synthesis of 5-Iodo-1-(sodium 2-deoxy-beta-D-ribofuranosyluronate)uracil and 5-Iodo-1-(sodium beta-D-ribofuranosyluronate)uracil.

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Abstract
5-Iodo-1-(sodium 2-deoxy-.beta.-D-ribofuranosyluronate)uracil and 5-iodo-1-(sodium .beta.-D-ribofuranosyluronate)uracil were synthesized through a sequence of steps involving two key transformations, i.e., iodonation in the 5-position of the uracil moiety, using iodine monochloride and triethylamine, and oxidation of the 5''-position of the ribose moiety to give the corresponding t-butyl ribofuranosyluronates in a single reaction step using pyridinium dichromate-acetic anhydride (PDCA) as oxidant in the presence of t-butyl alcohol. After removal of the protective groups the title compounds were obtained. 5-Iodo-2''-deoxyuridine (IDU) is a structural analogue to thymidine. This apparent similarity induces phosphorylation of the 5''-hydroxyl by a herpes virus induced enzyme, thymidine kinase. The resulting 5''-monophosphate is further enzymatically phosphorylated yielding the triphosphate which subsequently is incorporated into herpes virus DNA as well as cellular DNA of infected cells leading to miscoding and the synthesis of defective proteins. IDU is today a clinically used antiherpes drug even though its use is somewhat restricted due to its high general cell toxicity.