Design, synthesis and gelation studies of 4,6-O-butylidene-α,β-unsaturated-β-C-glycosidic ketones: application to plant tissue culture

Abstract

A series of α,β-unsaturated-β-C-glycosidic ketones was synthesized starting from D-glucose in three steps. 4,6-O-Butylidene-β-C-glycosidic ketones on aldol condensation with aromatic and heteroaromatic aldehydes in the presence of a suitable organocatalyst led to the stereoselective formation of the products in good yield. Hydrogen bonding and π–π stacking of these derivatives were established by single-crystal XRD. The soft material derived from this method had a diameter of 10–200 nm with a three-dimensional network, as determined by SEM and HR-TEM. In the present study, we discuss the mechanism of formation of these self-assembled nanostructures, the morphology of the soft material and its thermal stability. We also demonstrate the utility of these soft materials in the field of plant tissue culture.