183987-41-9Relevant academic research and scientific papers
Stereoselective synthesis of 3′-C-allyluridines and 3′-spiro-γ-lactone uridine analogues
Nielsen,Larsen,Wengel
, p. 1030 - 1035 (2007/10/03)
Grignard reactions of 3′-ketouridines 1a-e with allylmagnesium bromide and CeCl3 afforded novel 3′-C-allyluridines 2a-e and 3d-e. The diprotected 3′-keto nucleosides 1a-c afforded xylo-configurated compounds 2a-c and the 5′-unprotected 3′-keto nucleosides 1d-e afforded mixtures of xylo- and ribo-configurated compounds 2d/3d and 2e/3e. The allyluridine 2a was converted into the diol 4 by standard hydroboration and further oxidised to the 3′-spiro-γ-lactone nucleoside 5. This compound and its deprotected analogue 6 are the first examples of a novel class of 3′-spiro nucleoside analogues. Acta Chemica Scandinavica 1996.
