Fluorous-Assisted Synthesis of (E)-5-[3-Aminoallyl]-Uridine-5′-O-Triphosphate

Abstract

An efficient, reliable method for the chemical synthesis of (E)-5-[3-aminoallyl]-uridine-5′-O-triphosphate (AA-UTP), starting from 5-iodouridine, is described. This new strategy features the involvement of one-pot triphosphate formation and fluorous solid-phase extraction (F-SPE). The one-pot synthesis involves the mono phosphorylation of fluorous-tagged uridine, followed by the reaction with pyrophosphate to afford the fluorous-tagged AA-UTP. The F-SPE is achieved by installing a fluorous-tag onto the uridine prior to triphosphate formation, purification via F-SPE, and cleavage of the fluorous-tag. It is worth mentioning that this protocol produces AA-UTP in high yield and purity using one simple F-SPE; no conventional column chromatography is involved. © 2015 by John Wiley & Sons, Inc.