New highly soluble b-aminoalcohol b-cyclodextrin (b-CD) derivatives have been synthesized via nucleophilic epoxide opening reactions with mono-6-amino mono-6-deoxy-permethyl-b-CD and mono-6-amino mono-6-deoxy-b-CD. The binding properties of the b-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.
Synthesis of water-soluble multidentate aminoalcohol b-cyclodextrin derivatives via epoxide opening
ROSATI, Ornelio;CURINI, Massimo
2011
Abstract
New highly soluble b-aminoalcohol b-cyclodextrin (b-CD) derivatives have been synthesized via nucleophilic epoxide opening reactions with mono-6-amino mono-6-deoxy-permethyl-b-CD and mono-6-amino mono-6-deoxy-b-CD. The binding properties of the b-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.File in questo prodotto:
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