title: Complete sets of monosubstituted cyclomaltohexaoses (α-cyclodextrins) as precursors for further synthesis.
abstract: 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.
authors: Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic.
authors: Michal
authors: M
authors: Rezanka
authors: Jindřich
authors: J
authors: Jindřich
mesh_terms: D000107:Acetylation; D000447:Aldehydes / Q000138:chemical synthesis; D000478:Alkylation; D002264:Carboxylic Acids / Q000138:chemical synthesis; D002384:Catalysis; D019327:Copper Sulfate / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D017975:Ruthenium Compounds / Q000737:chemistry; D047391:alpha-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D017975:Ruthenium Compounds; D047391:alpha-Cyclodextrins; D019327:Copper Sulfate; C038365:ruthenium chloride