ARS | Publication request: Carbohydrate Green Chemistry: C-Glycoside Ketones as Potential Chiral Building Blocks

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: May 15, 2009
Publication Date: May 15, 2009
Citation: Carpenter, C.A., Kenar, J.A., Price, N.P. 2009. Carbohydrate Green Chemistry: C-Glycoside Ketones as Potential Chiral Building Blocks [abstract]. American Chemical Society. Abstract #47.

Technical Abstract: "Green chemistry" methods to produce new chemicals from renewable agricultural feedstocks will decrease our dependence on imported petroleum feedstocks and lower the environmental impact of consumer products. Our current research focuses on development of new carbohydrate-based derivatives, "locked ring" C-glycosides, and the subsequent formation of various functionalized ketohydrazones and oximes. The C-glycosides developed use ordinary monosaccharides as starting materials and are produced from aqueous-based, one-pot reactions. Furthermore, the functionalized C-glycosides retain a closed ring conformation of the parent sugars. Yields are nearly quantitative and no protecting group manipulations or activation of the anomeric center is needed. This poster describes how the C-glycosides may be used as chiral building blocks for molecules with potential applications as carbohydrate-based surfactants, detergents, liposomes, and bilayers.