Asymmetric Synthesis of 4′-Methyl-2′,3′-dideoxynucleosides

Abstract

The stereoselective preparation of a 4-methyl-2,3-dideoxyribose derivative is described which utilizes (-)-menthyl pyruvate as a chiral template and an organocerium addition as the key carbon-carbon bond-forming step. The 4-methyl-2,3-dideoxyribose derivative was used as a substrate for a Vorbrüggen pyrimidine glycosylation giving an α, β-mixture of 4′-methyl-2′,3′-dideoxynucleosides.