title: Synthesis of 3I-O and 2I-O-monosubstituted derivatives of per-6-azido-β-cyclodextrin-potential molecular scaffolds.
abstract: Alkylation of per-6-azido-β-cyclodextrin by a suitable electrophilic reagent (cinnamyl bromide or propargyl bromide) gave a mixture of 3(I)-O and 2(I)-O regioisomers. After peracetylation and chromatographic separation on silica gel, pure isomers were isolated. Oxidative cleavage of cinnamyl double bond afforded the corresponding formylmethyl and carboxymethyl derivatives. The prepared scaffold molecules are equipped with two types of reactive groups which have a potential to serve as points of attachment for various compounds.
authors.affiliation: Department of Organic and Nuclear Chemistry, Charles University in Prague, Faculty of Science, Hlavova 8, 128 40 Prague 2, Czech Republic.
authors.forename: Martin
authors.initials: M
authors.lastname: Popr
authors.forename: Simona
authors.initials: S
authors.lastname: Hybelbauerová
authors.forename: Jindřich
authors.initials: J
authors.lastname: Jindřich
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001386:Azides; D047392:beta-Cyclodextrins