5'-O-DMT-thymidine

5′-O-DMT-thymidine (5′-O-(4,4′-dimethoxytrityl)thymidine, DMTrT) is a modified nucleoside in which the 5′-hydroxyl group of thymidine is protected by an acid-labile dimethoxytrityl (DMTr) group.¹ ² This protecting group prevents undesired reactions during nucleoside manipulation and can be selectively removed under mild acidic conditions.¹ Due to this reversible protection, DMTrT is a fundamental intermediate in synthetic DNA chemistry and the controlled assembly of oligonucleotides.¹ ²

 

Applications

 

5′-O-DMT-thymidine is widely used in nucleic acid chemistry and drug development.¹ ² ³ ⁴ It functions as a key building block in oligonucleotide synthesis, where the DMTr group protects the 5′-hydroxyl during chain elongation and is selectively removed to enable stepwise nucleotide addition.¹ ³ DMTrT is also employed in large-scale, solution-phase synthesis using soluble supports, allowing efficient purification by precipitation.³ ⁴ Additionally, it serves as a precursor for modified nucleotides, including antiviral thiophosphoramidates and protected trinucleotide phosphoramidites used in gene synthesis and mutagenesis.² ³