A direct synthesis of 5-azidomethyl pyrimidine nucleosides via dehydroxyazidation

Abstract

We have successfully developed a direct azidation method for selectively functionalizing 5-hydroxymethyl pyrimidine deoxyribonucleosides (such as 5hmdU and 5hmdC) and nucleobases. This approach yielded the corresponding 5-azidomethyl nucleobases and nucleosides (5zmdU and 5zmdC) with moderate to good yields, eliminating the requirement for converting them into more reactive halides or tosylates beforehand. The incorporated azido group demonstrated effectiveness as a chemical tag for subsequent labeling and detection by reacting with strained alkyne DBCO-acid.