WATER-SOLUBLE CAVITANDS - SYNTHESIS OF METHYLENE-BRIDGED RESORCIN[4]ARENES CONTAINING HYDROXYLS AND PHOSPHATES AT THEIR FEET AND BROMOMETHYLS AND THIOMETHYLS AT THEIR RIMS

The synthesis of rim-functionalized methylene-bridged resorcin[4]arene s (''cavitands'') containing hydrophilic propanol or water-solublilizi ng propylphosphate feet is described. The cavitands possess the synthe tically useful benzylthiol (cavitands 6 and 16) or benzylbromide (cavi tands 9 and 11) functionalities at their rims, which are suitable for further derivatization near the hydrophobic cavity of the cavitand. Th ese water-soluble cavitands represent new building blocks that are ide al for use in aqueous supramolecular chemistry. As an example of their synthetic utility in supramolecular studies, we have reacted phosphat e-footed cavitands 11 and 16 with cysteine-containing peptide 17 and c hloroacetylated peptide 19, respectively, to afford the corresponding de novo proteins 18 and 20.