Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin-potential molecular scaffolds

Abstract

Alkylation of per-6-azido-β-cyclodextrin by a suitable electrophilic reagent (cinnamyl bromide or propargyl bromide) gave a mixture of 3(I)-O and 2(I)-O regioisomers. After peracetylation and chromatographic separation on silica gel, pure isomers were isolated. Oxidative cleavage of cinnamyl double bond afforded the corresponding formylmethyl and carboxymethyl derivatives. The prepared scaffold molecules are equipped with two types of reactive groups which have a potential to serve as points of attachment for various compounds.