Nucleoside Annelating Reagents: N-(tert-Butyloxycarbonyl)-2-bromoacetamide and 2-Chloroketene Diethyl Acetal

Article abstract of DOI:10.1021/jo00214a015

The title reagents undergo cyclocondesation reaction with the amidine-like moiety of tri-O-acetyladenosine and cytidine (and related compounds) to form a new five-membered ring (etheno bridging), substituted with a (tert-butoxycarbonyl)amino or an ethoxy function.Some of the products exhibit useful fluorescence properties.Removal of the tert-butoxycarbonyl group with standard conditions gives the corresponding, somewhat unstable amino compounds which can be conveniently characterized as the corresponding N-acetyl derivatives.The reagents introducing additional substitution on the etheno bridge, with enhanced fluorescence, also suggest the possibility of cross-linking functionalization.