title: Sugar-pendant diamines.
abstract: A set of 1,3-propanediamine derivatives connected to carbohydrates (5) has been prepared in four steps from peracetylated sugar and 1,3-dibromo-2-propanol in 60-73% yields. D-Glucose, D-mannose, D-galactose, D-xylose, D-ribose, and maltose are utilized as sugar molecules in this work. The diamine moiety was connected to the C1 carbon of the glycopyranose ring via an O-glycoside bond. All of the anomeric configurations and sugar puckering conformations, except in the D-maltose derivative, were determined by X-ray crystallography of the diazido or dibromo precursors. While glycosidation of peracetylated galactopyranose with 1,3-dibromo-2-propanol in the presence of boron trifluoride afforded both anomers, the neighboring group participation of the 2-acetoxy group yielded a single anomer for the other substrates. This method has been used to synthesize a library of sugar-pendant diamines including an OH-protected derivative (6), and an N,N'-diisopropyl-substituted derivative (7). A similar series of reactions using 2,3-dibromo-1-propanol gave ethylenediamine-type derivatives (11), and bis(bromomethyl)bis(hydroxymethyl)methane (12) gave bisglucose-pendant derivatives (16).
authors.affiliation: Department of Chemistry, Faculty of Science, Nara Women's University, Nara 630-8506, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Mikata
authors.forename: Y
authors.initials: Y
authors.lastname: Shinohara
authors.forename: K
authors.initials: K
authors.lastname: Yoneda
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authors.initials: Y
authors.lastname: Nakamura
authors.forename: K
authors.initials: K
authors.lastname: Esaki
authors.forename: M
authors.initials: M
authors.lastname: Tanahashi
authors.forename: I
authors.initials: I
authors.lastname: Brudziñska
authors.forename: S
authors.initials: S
authors.lastname: Hirohara
authors.forename: M
authors.initials: M
authors.lastname: Yokoyama
authors.forename: K
authors.initials: K
authors.lastname: Mogami
authors.forename: T
authors.initials: T
authors.lastname: Tanase
authors.forename: T
authors.initials: T
authors.lastname: Kitayama
authors.forename: K
authors.initials: K
authors.lastname: Takashiba
authors.forename: K
authors.initials: K
authors.lastname: Nabeshima
authors.forename: R
authors.initials: R
authors.lastname: Takagi
authors.forename: M
authors.initials: M
authors.lastname: Takatani
authors.forename: T
authors.initials: T
authors.lastname: Okamoto
authors.forename: I
authors.initials: I
authors.lastname: Kinoshita
authors.forename: M
authors.initials: M
authors.lastname: Doe
authors.forename: A
authors.initials: A
authors.lastname: Hamazawa
authors.forename: M
authors.initials: M
authors.lastname: Morita
authors.forename: F
authors.initials: F
authors.lastname: Nishida
authors.forename: T
authors.initials: T
authors.lastname: Sakakibara
authors.forename: C
authors.initials: C
authors.lastname: Orvig
authors.forename: S
authors.initials: S
authors.lastname: Yano
mesh_terms: D002240:Carbohydrate Sequence; D003959:Diamines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
chemical_list: D003959:Diamines; D007202:Indicators and Reagents; D009844:Oligosaccharides