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

Lemaire, Sébastien; Houpis, Ioannis; Wechselberger, Rainer; Langens, Jaak; A. A. Vermeulen, Wim; Smets, Nico; Nettekoven, Ulrike; Wang, Youchu; Xiao, Tingting; Qu, Haisheng; Liu, Renmao; Jonckers, Tim H.M.; Raboisson, Pierre; Vandyck, Koen; Nilsson, Karl M.; Farina, Vittorio

doi:10.1021/jo101822j.s001

jo101822j_si_001.pdf (3.44 MB)

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

journal contribution

posted on 2011-01-07, 00:00 authored by Sébastien Lemaire, Ioannis Houpis, Rainer Wechselberger, Jaak Langens, Wim A. A. Vermeulen, Nico Smets, Ulrike Nettekoven, Youchu Wang, Tingting Xiao, Haisheng Qu, Renmao Liu, Tim H.M. Jonckers, Pierre Raboisson, Koen Vandyck, Karl M. Nilsson, Vittorio Farina

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.