Complete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis

TitleComplete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis
Publication TypeJournal Article
Year of Publication2013
AuthorsBláhová M, Bednářová E, Řezanka M, Jindřich J
JournalThe Journal of Organic Chemistry
Volume78
Issue2
Pagination697 - 701
Date Published2013/01/18/
ISBN Number0022-3263
Keywordsduplicate
AbstractRegioselective alkylation of ?-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 2I-O-, 3I-O- and 6I-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2I-O-, 3I-O-, and 6I-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of ?-cyclodextrin.
URLhttp://dx.doi.org/10.1021/jo301656p
Short TitleJ. Org. Chem.
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