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Complete sets of monosubstituted γ-cyclodextrins as precursors for further synthesis

Complete sets of monosubstituted γ-cyclodextrins as precursors for further synthesis

Journal of Organic Chemistry 78(2): 697-701

Regioselective alkylation of γ-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation of the remaining hydroxyl groups and separation of isomers resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2(I)-O-, 3(I)-O-, and 6(I)-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of γ-cyclodextrin.

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Accession: 052260520

Download citation: RISBibTeXText

PMID: 23205761

DOI: 10.1021/jo301656p

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