Abstract
A dioxane homo-sugar analog, (2S,5S)-and (2R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-iodomethyl-1,4-dioxane was prepared from (2R,3R)-dimethyl tartrate, and further elaborated into the corresponding homo-N-nucleoside analogs by its reactions with uracil and adenine, respectively.
Highlights
There has been an increasing interest in the synthesis of nucleoside analogs with modifications of the sugar moiety for the purpose of obtaining new antiviral and antitumor agents [1,2,3]
We decided to pursue the synthesis of nucleoside analogs, based on the conformationally more flexible, optically active homo-1,4-dioxane sugar analogs
A representative structure is shown in Figure 1, where the 1,4-dioxane homosugar analog is substituted with uracil or adenine, respectively
Summary
There has been an increasing interest in the synthesis of nucleoside analogs with modifications of the sugar moiety for the purpose of obtaining new antiviral and antitumor agents [1,2,3]. The residue was purified by flash chromatography (CHCl3/CH3OH, 9:1 mixture) to give 0.83 g, 26 % of the pure product 2.
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