Synthesis of a Novel, Optically Active Uridine Analog Containing a 1,4-Dioxane Sugar Moiety. Synthesis of the Corresponding Dinucleotide

Abstract

A new optically active uridine nucleoside analogue in which a substituted 1,4-dioxane ring functioned as the sugar analogue was prepared from L-tartaric acid. The nucleoside analogue was further converted into the corresponding protected dinucleotide.

Synthesis of Novel Homo-N-Nucleoside Analogs Composed of a Homo-1,4-Dioxane Sugar Analog and Substituted 1,3,5-Triazine Base Equivalents

“…Rather than applying the five-membered sugars found in the natural nucleosides, we targeted on the application of the more robust and more flexible sugar analogs containing the 1,4-dioxane moiety, for example compound 1 , whose synthesis has been reported in a previous publication [ 32 ]. Compound 1 , containing an unnatural sugar analog may also prove to be robust in biologic systems, as enzymes may not find pathways to convert the unnatural nucleoside system.…”