Synthesis of oligodeoxyribonucleotides involving a rapid procedure for removal of base-protecting groups by use of the 4,4′,4″-tris(benzoyloxy)trityl (TBTr) group

Abstract

Fully protected building units for oligodeoxyribonucleotide synthesis in the phosphoramidite approach were prepared in high yields by the 5′-dimethoxytritylation of N-[4,4′,4″-tris(benzoyloxy)trityl]deoxyribonu-cleosides followed by the 3′-phosphitylation with methoxymorpholinochlorophosphine. The solid phase synthesis of oligodeoxyribonucleotides on a controlled pore glass gel using the amidite units was examined. The efficiency of condensation was discussed in detail. The 4,4′,4″-tris(benzoyloxy)trityl (TBTr) group was removed rapidly from a protected tetramer synthesized on the controlled pore glass gel to give dGpCpApT.