179026-52-9Relevant 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.
New method for the preparation of 3'- and 2'-phosphoramidites of 2'- and 3'-difluoromethyleneuridine
Serafinowski,Barnes
, p. 7929 - 7938 (2007/10/03)
The one step reaction of 2'- and 3'-keto derivatives of uridine 2a, 2b, 7a and 7b with bromodifluoromethyl[tris(dimethylamino)]phosphonium bromide (13) and zinc gives the corresponding 2'- and 3'-difluoromethylene nucleosides 3a, 3b, 8a and 8b in good yield. Removal of the silyl groups affords difluoromethylenated uridines 4a, 4b, 9a and 9b. Phosphitylation of 4a and 9a provides the target 2'- and 3'-phosphoramidites 5 and 10 for use in oligonucleotide synthesis.
