An Efficient One-pot N-Acylation of Deoxy- and Ribo-cytidine Using Carboxylic Acids Activated in situ with 2-Chloro-4,6-dimethoxy-1,3,5-triazine

摘要

Synthetic oligonucleotides (ODNs) are an emerging class of drug molecules with a broad spectrum for therapeutic applications. In the ODNs synthesis, a fundamental process is the internucleotide-bond formation achieved via the condensation of a nucleoside and a suitably activated nucleoside such as the phosphoryl, H-phosphoryl, or phosphoramidite species. In this step, when the substances without the protection of the nucleo-base are used, the exocyclic amino group of the adenine and cytosine moieties, and sometimes that of the guanine moiety, undergoes undesired modification. Accordingly, protection of the amino function is required to achieve the desired inter-nucleotide linkage construction. Thus, the invention of amino protection is one of the most important research topics in nucleotide synthesis.