title: Efficient regioselective O3-monodesilylation by hydrochloric acid in cyclodextrins.
abstract: An efficient O3-monodesilylation method has been developed for the derivatization of per-3-O-silylated cyclodextrin (CD) derivatives. Using hydrochloric acid as a reagent, the O3-monodesilylation was found to be regioselective, mild, practical and general as it can be applied to all α-, β- and γ-CDs. The advantage of the methodology is that the acid-catalyzed O3-desilylation can be carried out in a stepwise manner so that different types of functional groups can be introduced to a CD molecule at different stage of the O3-desilylations. This makes the current methodology flexible and versatile. This current methodology constitutes one of the few methodologies available for the regioselective modification of CDs at the secondary face.
authors.affiliation: Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada.
authors.forename: Jiamin
authors.initials: J
authors.lastname: Gu
authors.affiliation: Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada.
authors.forename: Tong
authors.initials: T
authors.lastname: Chen
authors.affiliation: Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada.
authors.forename: Qifang
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada.
authors.forename: Tieyu
authors.initials: T
authors.lastname: Chen
authors.affiliation: Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta T2N 1N4, Canada. Electronic address: ccling@ucalgary.ca.
authors.forename: Chang-Chun
authors.initials: CC
authors.lastname: Ling
mesh_terms: D002384:Catalysis; D006851:Hydrochloric Acid / Q000737:chemistry*; D017665:Hydroxyl Radical / Q000737:chemistry*; D047391:alpha-Cyclodextrins / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*; D047408:gamma-Cyclodextrins / Q000737:chemistry*
chemical_list: D047391:alpha-Cyclodextrins; D047392:beta-Cyclodextrins; D047408:gamma-Cyclodextrins; D017665:Hydroxyl Radical; D006851:Hydrochloric Acid
keywords: Cyclodextrins; Hydrochloric acid; O3-Desilylation; Regioselectivity; Silyl protecting group