DIBAL-H-mediated O-desilylation with highly sterically hindered cyclodextrin substrates

DIBAL-H-mediated desilylation reaction has been extended to sterically even more hindered 6-O-thexyldimethylsillyl-2,3-di-O-alkyl protected CD substrates. It was found the reductive desilylations are still regioselective to afford the 6A- and 6A,6D-O-didesilylated products. By changing the amount of reagent used, each of the products can be isolated as a majority. The alkyl groups appear to be compatible with methyl, benzyl, and even the more versatile allyl groups.