Synthesis of 2'-Methyl-6-methoxyguanosine from the Parent Ribonucleoside Guanosine

J Org Chem. 2019 Apr 19;84(8):4646-4652. doi: 10.1021/acs.joc.8b02194. Epub 2018 Oct 11.

Abstract

A short and efficient synthesis of the nucleoside fragment contained in the NS5B nucleoside inhibitor BMS-986094 was achieved in 23% overall yield on a gram scale. The synthesis uses the widely available starting material guanosine via a short sequence ending in a Mukaiyama hydration reaction to establish the key tertiary alcohol moiety and set the C-2' methyl stereogenic center. This work resulted in a robust and scalable approach to this complex nucleoside.

MeSH terms

  • Guanosine / analogs & derivatives
  • Guanosine / chemistry*
  • Molecular Structure

Substances

  • Guanosine