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General synthesis of sugar-pendant 1,3-propanediamines containing aC-glycoside linkage

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
48
Identifiers
DOI: 10.1016/j.tetlet.2004.10.006
Keywords
  • Carbohydrates
  • C-Glycoside
  • 1
  • 3-Propanediamine
  • Malononitrile
  • Sugar-Pendant

Abstract

Abstract A straightforward route to C-glycoside linked sugar-pendant 1,3-propanediamines is described. The three-step preparation procedure involves (1) C-glycosylation of an OH-protected α-glycosyl halide with malononitrile, (2) catalytic hydrogenation of the nitriles to amines, and (3) deprotection of acetyl groups via acid-catalyzed hydrolysis. In the case of the galactose derivative, excess sodiomalononitrile promotes the second addition of a carbanion in the first step. The β-anomeric configuration was confirmed by X-ray crystallography of the glycosylated intermediates. This method demonstrates a general method to access a new class of carbohydrate-pendant C-glycoside chelators.

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