Saccharide Recognition by a Three Arm-Shaped Host Having Preorganized Three-Dimensional Hydrogen-Bonding Sites.

Generally, cage-shaped hosts for saccharides can strongly bind to guest molecules owing to the three-dimensional preorganized hydrogen-bonding sites. However, the preparation of cage molecules is often difficult due to the low-yield macrocyclization step. Here, we report a three arm-shaped molecule possessing pyridine-acetylene-phenol units as a new kind of host having a preorganized three-dimensional hydrogen-bonding site. This three arm-shaped host was readily prepared compared to a cage-shaped analogue. This host associated with lipophilic glycosides to form chiral complexes, and the association constants were sufficiently high as well as those of the cage-shaped one. Furthermore, this host extracted native monosaccharides into a lipophilic solvent.