| Abstract
| - A set of 1,3-propanediamine derivatives connected to carbohydrates (5) has been prepared in foursteps 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 diaminemoiety was connected to the C1 carbon of the glycopyranose ring via an O-glycoside bond. All ofthe 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 glycosidationof peracetylated galactopyranose with 1,3-dibromo-2-propanol in the presence of boron trifluorideafforded both anomers, the neighboring group participation of the 2-acetoxy group yielded a singleanomer for the other substrates. This method has been used to synthesize a library of sugar-pendantdiamines 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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