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Abstract
Enantioselective syntheses from dimethyl tartrate of 1,3,5-triazine homo-N-nucleoside analogs, containing a 1,4-dioxane moiety replacing the sugar unit in natural nucleosides, were accomplished. The triazine heterocycle in the nucleoside analogs was further substituted with combinations of NH2, OH and Cl in the 2,4-triazine positions.
Highlights
Nucleoside analogs represent a potentially important class of medicinal active agents that have found uses in antitumor and antiviral drugs [1]
The presence of s-triazines was interesting, since the various 1,3,5-triazines can be formed from hydrogen cyanide, ammonia and water, components believed to be plentiful in the primordial soup
Considering the potential applications of the 1,3,5-triazine based systems, surprisingly few triazine nucleoside analogs or triazine glycosides have been reported in the literature [27,28,29,30,31]. For these reasons we found it viable to initial a study of the synthesis of triazine based nucleoside analogs
Summary
Nucleoside analogs represent a potentially important class of medicinal active agents that have found uses in antitumor and antiviral drugs [1]. The 3,5-diaminotriazine homo-N-nucleoside analogs 8a and 8b were prepared by the reaction of the amino sugar analogs 5a and 5b respectively with 2-chloro-4,6-diaminotriazine in DMF in the presence of triethylamine. Trans-amine 5a afforded the desired diamino triazine homo-N-nucleoside analog 8a in 39 % yield.
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