Synthesis of a novel dioxane nucleoside having two bases, 2(R)-(5-fluouracil-1-yl)-5(R)-hydroxymethyl-3(R)(-uracil-1-yl)-1,4-dioxane and its 2(S)-isomer, from uridine

Article abstract of DOI:10.1016/S0040-4039(97)01613-4

A novel dioxane nucleoside for chemotherapy, 2(R)-(5-fluorouracil-1-yl)5(R)-hydroxymethyl-3(R)-(uracil- 1-yl)-1,4-dioxane and its 2(S)-isomer, were conveniently synthesized from uridine with several steps including periodate oxidation, partial reduction to form hemiacetals, and glycosidation of the second base, 5-fluorouracil, using stannic chloride as the catalyst.