title: Anti versus syn opening of epoxides derived from 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine with Me3Al: factors controlling the stereoselectivity.
abstract: Upon epoxidation with dimethyldioxirane, the 2',5'-bis-O-silyl derivatives of 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine gave the respective "3',4'-up" epoxides exclusively. Reaction between these epoxides and Me3Al was investigated in detail. It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature. A possible reaction mechanism is proposed.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Kubota
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Haraguchi
authors.forename: Mayumi
authors.initials: M
authors.lastname: Kunikata
authors.forename: Mari
authors.initials: M
authors.lastname: Hayashi
authors.forename: Masaomi
authors.initials: M
authors.lastname: Ohkawa
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Tanaka
mesh_terms: D017607:Aluminum Compounds / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D017607:Aluminum Compounds; D004852:Epoxy Compounds