title: Regioselective allylation of cyclomaltoheptaose (β-cyclodextrin) leading to per(2,6-di-O-hydroxypropyl-3-O-methyl)-β-cyclodextrin.
abstract: The selective modification of cyclodextrins remains a real challenge to obtain well-defined structures. The targeted cycloheptakis-(1→4)-2,6-di-O-hydroxypropyl-3-O-methyl-α-D-glucopyranosyl [per(2,6-di-O-hydroxypropyl-3-O-methyl)-β-CD] was obtained by a three-step procedure. The selective allylation of the hydroxyl functions at the positions 2 and 6 was used as a first step. This reaction was revisited then enlarged to α and γ-CDs to determine new conditions for a one-step synthesis in high yield. The per(2,6-di-O-allyl)-β-CD derivative was then reacted with iodomethane to provide per(2,6-di-O-allyl-3-O-methyl)-β-CD. Oxidative hydroboration of the allyl functions was then carried out in order to obtain a new CD derivative with seven primary hydroxyl functions on each side of the truncated cone, having a similar reactivity.
authors.affiliation: Laboratoire d'Analyse et de Modélisation pour la Biologie et l'Environnement, UMR8587 UEVE-CNRS-CEA, Bld François Mitterrand, 91025 EVRY Cedex, France.
authors.forename: Zahra
authors.initials: Z
authors.lastname: Eskandani
authors.forename: Cécile
authors.initials: C
authors.lastname: Huin
authors.forename: Philippe
authors.initials: P
authors.lastname: Guégan
mesh_terms: D000465:Algorithms; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D005027:Ethylene Oxide / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D058105:Polymerization; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
chemical_list: D000498:Allyl Compounds; D047392:beta-Cyclodextrins; D005027:Ethylene Oxide; C031215:betadex