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Sugar-pendant diamines

TitleSugar-pendant diamines
Publication TypeJournal Article
Year of Publication2001
AuthorsMikata, 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
JournalJournal of Organic Chemistry
Volume66
Pagination3783-3789
Date PublishedJun
Type of ArticleArticle
ISBN Number0022-3263
KeywordsBINDING-PROPERTIES, C-2 EPIMERIZATION, CARBON SKELETON, D-GLUCOSE, ETHYLENEDIAMINE, LIGANDS, N-GLYCOSIDES, NICKEL(II) COMPLEXES, PHOTOCYTOTOXICITY, WATER
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).

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