Reactions designed for primary face modification are typically unsuitable for the less reactive secondary hydroxyls, so our synthetic strategies are optimized for the secondary face. We take mono-3-amino-βcyclodextrin (3-NH2-β-CD) as a starting point. Its synthesis is well documented , its amino group is more reactive than the hydroxyls, and chemo-selective reactions directed towards the amine eliminate the large number of products often produced upon direct functionalization of the hydroxyls. Nonetheless, adoption of this starting material does not resolve critical challenges of reactivity and purification. The synthetic strategies described here thus are based on several key observations and approaches, as follows.