ol402143y_si_002.pdf (14.04 MB)
An Alternative Pathway to Ribonucleoside β‑Hydroxyphosphonate Analogues and Related Prodrugs
journal contribution
posted on 2016-02-18, 20:53 authored by Audrey Hospital, Maïa Meurillon, Suzanne Peyrottes, Christian PérigaudNucleoside β-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5′-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of a β-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.