Complete sets of monosubstituted cyclomaltohexaoses (α-cyclodextrins) as precursors for further synthesis

Alkylation of cyclomaltohexaose (α-cyclodextrin, α-CD) with allyl or cinnamyl bromide, followed by peracetylation of remaining hydroxyl groups and separation of isomers, resulted in the set of peracetylated 2I-O-, 3I-O- and 6I-O-alkylated α-CDs in up to 27% yields. Ozonolysis or oxidative cleavage of peracetylated allyl or cinnamyl derivatives resulted in a complete set of peracetylated 2I-O-, 3I-O- and 6I-O-formylmethyl or carboxymethyl derivatives that are useful precursors for preparation of regioselectively monosubstituted derivatives of α-CD. Moreover, a quick method to recognize single 2I-O-, 3I-O- and 6I-O-monosubstituted peracetylated CDs from one another using only their 1H NMR spectra has been proposed.

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