First organocatalytic, diastereoselective synthesis of tRNA wobble nucleosides: (R)- and (S)-methoxycarbonylhydroxymethyluridines (mchm5Us) and their acid analogues (chm5Us)

Abstract

A diastereoselective organocatalytic synthesis of (R)- and (S)-methoxycarbonylhydroxymethyluridines (mchm⁵Us) and their acid analogues (chm⁵Us) was developed. The method employs organo- and organometallic-catalyzed cyanosilylation of 5-formyluridine to yield diastereomerically enriched TMS-protected cyanohydrins, which are converted via a Pinner reaction to (R)- and (S)-mchm⁵Us, then hydrolyzed to (R)- and (S)-chm⁵Us.