Reactions of dimesylthymidine with secondary amines: Easy access to 3′,5′-dideoxy-3′-substituted-5′-alkylaminothymidines - New classes of potential antiviral aminonucleosides.

Add time:07/28/2019    Source:sciencedirect.com

3′,5′-Di-O-mesylthymidine 4a (DMST) on reaction with secondary amines undergoes hitherto unknown “one-pot-two-steps” transformation to produce 2,3′-O-anhydro-5′-deoxy-5′-alkylaminothymidines 5a–h. Most of the amines used, irrespective of their basicities showed remarkable selectivity towards the 5′-substitution over the 2,3′-O-anhydro ring formation. Compounds 5a–h could be used as intermediates for the synthesis of a variety of 3′,5′-dideoxy-3′-substituted-5′-alkylaminothymidines of the type 9, 10a–b, 11.

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