An Undergraduate Organic Chemistry Laboratory Experiment: The Multistep Synthesis of a Modified Nucleoside

Abstract

We have designed and integrated the multistep synthesis of a modified nucleoside into an undergraduate organic chemistry laboratory. The laboratory was designed as a multidisciplinary approach towards a single synthetic problem. Here we report the synthesis and subsequent purification of 5'-O-dimethoxytrityl-2'-O-methyluridine and 5'-O-dimethoxytrityl-3'-O-methyluridine directly from the literature by a protocol that is appropriate in a small school setting.