Synthesis of per-2,3-di-O-heptyl-β and γ-cyclodextrins: a new kind of amphiphilic molecules bearing hydrophobic parts

The synthesis of per-2,3-di-O-heptyl-β and γ-cyclodextrins, a new kind of amphiphilic cyclodextrins bearing long and stable hydrophobic chains is described. The products are obtained in a three-step synthesis from natural cyclodextrins in good yield. tert-Butyldimethylsilyl protection of the primary hydroxyl group was found to be stable under the basic conditions required for the nucleophilic substitution of the bromine derivatives. The structure of the new amphiphilic molecules was proved by NMR spectroscopy and mass spectrometry (ESI-MS or MALDI-TOF-MS).