title: Synthesis of water-soluble multidentate aminoalcohol β-cyclodextrin derivatives via epoxide opening.
abstract: New highly soluble β-aminoalcohol β-cyclodextrin (β-CD) derivatives have been synthesized via nucleophilic epoxide opening reactions with mono-6-amino mono-6-deoxy-permethyl-β-CD and mono-6-amino mono-6-deoxy-β-CD. The binding properties of the β-CD were enhanced by linking aminoalcohol subunits which caused its solubility to improve markedly. The reaction conditions were optimised using microwave irradiation giving moderate-to-good yields with a series of epoxides. A regioselective epoxide opening reaction was observed in the reaction with styrene oxide while the stereoselectivity was strictly dependent on substrate structure.
authors: Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Via P. Giuria 9, 10125 Torino, Italy.
authors: K
authors: K
authors: Martina
authors: M
authors: M
authors: Caporaso
authors: S
authors: S
authors: Tagliapietra
authors: G
authors: G
authors: Heropoulos
authors: O
authors: O
authors: Rosati
authors: G
authors: G
authors: Cravotto
mesh_terms: D000475:Alkenes / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D005026:Ethylene Glycols / Q000737:chemistry; D008872:Microwaves; D012995:Solubility; D012997:Solvents / Q000737:chemistry*; D014867:Water / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; D005026:Ethylene Glycols; D012997:Solvents; D047392:beta-Cyclodextrins; D014867:Water