title: Complete sets of monosubstituted γ-cyclodextrins as precursors for further synthesis.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic.
authors.forename: Markéta
authors.initials: M
authors.lastname: Bláhová
authors.forename: Eva
authors.initials: E
authors.lastname: Bednářová
authors.forename: Michal
authors.initials: M
authors.lastname: Řezanka
authors.forename: Jindřich
authors.initials: J
authors.lastname: Jindřich
mesh_terms: D000478:Alkylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D047408:gamma-Cyclodextrins; D010293:Pargyline; C458239:propargyl bromide