ABSTRACT
Cyclomaltoheptaose or ß-cyclodextrin (ß-CD) is a naturally occurring cyclooligosaccharide composed of seven a-(1–4)-linked d-glucopyranose units. ß-CD has become a valuable building block for a variety of nanodevices which operate through the entrapment of organic molecules in water, such as molecular sensors, switches, and delivery systems.1–6 Many ß-CD applications require the covalent linkage of one or more functional appendages on its structure to provide biological, photochemical, catalytic, or redox abilities. The chapter discusses the synthesis of 2-O-propargylcyclomaltoheptaose 2 as a convenient building block for the construction of ß-CD derivatives functionalized on the secondary face. The terminal alkyne group offers the possibility to attach a variety of appendages. Compound 2 can be prepared directly from native ß-CD 1 without using protecting groups, by treatment with propargyl bromide and a judiciously measured amount of lithium hydride in dry DMSO in the presence of catalytic lithium iodide.
