An efficient and large-scale enantioselective synthesis of PNP405: a purine nucleoside phosphorylase inhibitor.

@article{Prashad2002AnEA,
  title={An efficient and large-scale enantioselective synthesis of PNP405: a purine nucleoside phosphorylase inhibitor.},
  author={Mahavir Prashad and Denis Har and Lijian Chen and Hongyong Kim and Oljan Repi{\vc} and Thomas J. Blacklock},
  journal={The Journal of organic chemistry},
  year={2002},
  volume={67 19},
  pages={
          6612-7
        }
}
An efficient and large-scale enantioselective synthesis of PNP405 (1), a purine nucleoside phosphorylase inhibitor, is described. This synthesis of 1 involved eight steps starting from o-fluorophenylacetic acid with a 21.6% overall yield and >99.5% enantiopurity. The key stereogenic center with (R)-configuration was created using Evans' asymmetric alkylation methodology. This synthesis also features the racemization-free reductive removal of the chiral auxiliary in 5 using sodium borohydride… Expand
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