Calixcyclitols: a new class of polar hybrid hosts obtained by oxygenation of calixarene phenol rings.

The first examples of hybrid calixarene hosts containing cyclitol moieties (calixcyclitols) have been obtained by treatment with LiAlH4 of diepoxydiol and tetraepoxytetrol calix[4]arene derivatives. A 6-oxabicyclo[3:1:1]heptanetriol or a cyclohexanetetrol ring was obtained depending on the stereochemical features of the diepoxydiol moiety. Preliminary binding studies toward anionic guests showed a discrete selectivity of calixcyclitol 9 vs H2PO4-.