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

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

Carbohydrate Research 346(15): 2374-2379

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 2(I)-O-, 3(I)-O- and 6(I)-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 2(I)-O-, 3(I)-O- and 6(I)-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 2(I)-O-, 3(I)-O- and 6(I)-O-monosubstituted peracetylated CDs from one another using only their (1)H NMR spectra has been proposed.

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Accession: 052260519

Download citation: RISBibTeXText

PMID: 21907975

DOI: 10.1016/j.carres.2011.08.011

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