Efficient regioselective O3-monodesilylation by hydrochloric acid in cyclodextrins

• Per-3-O-silylated cyclodextrin substrates have been monodesilylated with HCl
• The methodology is generally applicable to all α-, β- and γ-cyclodextrins
• We further developed a stage-wise O3-desilylation methodology
• A strategy for multi-functionalization of cyclodextrins has been demonstrated

An efficient O3-monodesilylation method has been developed for the derivatization of per-3-O-silylated cyclodextrin (CD) derivatives. Using hydrochloric acid as a reagent, the O3-monodesilylation was found to be regioselective, mild, practical and general as it can be applied to all α-, β- and γ-CDs. The advantage of the methodology is that the acid-catalyzed O3-desilylation can be carried out in a stepwise manner so that different types of functional groups can be introduced to a CD molecule at different stage of the O3-desilylations. This makes the current methodology flexible and versatile. This current methodology constitutes one of the few methodologies available for the regioselective modification of CDs at the secondary face.

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