Multicomponent diversity oriented synthesis of multivalent glycomimetics containing hexafluorovaline

The chemoselective introduction of fluorinated moieties into biologically relevant scaffolds is now an established strategy to modulate and to study the properties of molecular leads. In this article we propose, for the first time, the diversity oriented synthesis of multivalent glycomimetics incorporating hexafluorovaline through a straightforward multicomponent sequential process, which occurs with high yield and in mild conditions. The same process has been successfully applied to the chemistry of aminoglycosides producing a neomycin-hexafluorovaline-galactose conjugate and providing a general, efficient strategy to functionalized aminoglycosides with sugar-hexafluorovaline tags. (C) 2015 Elsevier Ltd. All rights reserved.