C-glycosides are a growing interest in synthetic chemistry for their use in the pharmaceutical industry as important drug pharmacophores and their potential use in chemical industry as surfactants. Previous literature describes the synthesis of C-glycosides using many steps and toxic reagents, often involving the use of protecting groups. The extra steps result in lower yields, require more reagents and produce more waste, which limits the environmental sustainability of the overall synthesis. This study aimed to reproduce the literature synthesis of β-C-glycosidic ketones from acetylacetone and monosaccharides without the use of protecting groups. These ketones were further reacted in aldol condensations with non-enolizable aldehydes. We probed the scope of this reaction with unprotected disaccharides, and reacted the products with hydroxymethylfurfural, a renewable bio-based platform molecule, in aldol condensation reactions. The results of our investigation will be presented.
Chiaramonte, Jon, "Synthesis of β-c-glycosidic Ketones from Unprotected Sugars and Their Use in Aldol Condensations with Hydroxymethylfurfural" (2020). Student Scholars Day Posters. 9.