Regioselective O2′,O3′‐Deacetylations of Peracetylated Ribonucleosides by Using Tetra‐n‐butylammonium Fluoride

A robust, mild, and highly regioselective deacetylation of 1,2‐diol diacetates in the presence of other acetate functions was achieved by using tetra‐n‐butylammonium fluoride. This method provided a single‐step route to access O5′‐acetyl ribonucleosides, a key intermediate in the synthesis of biomedically important nucleosides and nucleotides. Moreover, it offered the general applicability of a non‐enzymatic method for the selective deacetylation of peracetylated 2′‐deoxyribonucleosides. Its synthetic utility was further demonstrated by the synthesis of molecules of biomedical interest by using this particular deacetylation reaction.