Practical Synthesis of (2′R)-2′-Deoxy-2′-C-methyluridine by Highly Diastereoselective Homogeneous Hydrogenation

Diastereoselective hydrogenation of 2'-deoxy-2'-exo-methyleneuridine was carried out under homogeneous conditions using a low loading of a chiral Rh catalyst. This, coupled with improvements in the synthesis of the substrate, allowed the smooth pilot plant preparation of the title compound on >10 kg scale.