New synthesis of 3′-c-substituted-3′-nitromethyl-ribo-thymidines

Article abstract of DOI:10.1016/S0040-4020(01)86711-9

The 3′-exo-nitromethylene function in ribo-thymidine, as in 3, has been used for the first time as a general intermediate in the Michael addition reaction to give varieties of 3′-C-substituted nucleosides (12 - 21). The reaction of the conjugate base of acetylacetone with 3 however gave cis-fused furanose[3.2.1]hexopyranose nucleoside 24 as a major product due to the base catalyzed rearrangement of the initially formed Michael adduct 17. Detailed NMR spectroscopic data have been presented in support of the structural integrity of all reaction products.