|Publication Type||Journal Article|
|Year of Publication||2001|
|Authors||Mikata, Y, Shinohara, Y, Yoneda, K, Nakamura, Y, Esaki, K, Tanahashi, M, Brudzinska, I, Hirohara, S, Yokoyama, M, Mogami, K, Tanase, T, Kitayama, T, Takashiba, K, Nabeshima, K, Takagi, R, Takatani, M, Okamoto, T, Kinoshita, I, Doe, M, Hamazawa, A, Morita, M, Nishida, F, Sakakibara, T, Orvig, C, Yano, S|
|Journal||Journal of Organic Chemistry|
|Type of Article||Article|
|Keywords||BINDING-PROPERTIES, C-2 EPIMERIZATION, CARBON SKELETON, D-GLUCOSE, ETHYLENEDIAMINE, LIGANDS, N-GLYCOSIDES, NICKEL(II) COMPLEXES, PHOTOCYTOTOXICITY, WATER|
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).
|URL||<Go to ISI>://000168911300018|