A short path synthesis of [13C/15N] multilabeled pyrimidine nucleosides starting from glucopyranose nucleosides.

Irene M Lagoja (1) , Sylvie Pochet (2) , Valerie Boudou (1) , Roy Little (1) , Eveline Lescrinier (1) , Jef Rozenski (1) , Piet Herdewijn (1)

1 Laboratory for Medicinal Chemistry
2 Chimie Organique

The synthesis of fully [13C/15N] labeled pyrimidine nucleosides has been achieved from 13C-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of 13C-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.

Irene M Lagoja, Sylvie Pochet, Valerie Boudou, Roy Little, Eveline Lescrinier, et al.. A short path synthesis of [13C/15N] multilabeled pyrimidine nucleosides starting from glucopyranose nucleosides.. Journal of Organic Chemistry, 2003, 68 (5), pp.1867-71. ⟨10.1021/jo0205098⟩. ⟨pasteur-00166200⟩