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A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

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journal contribution
posted on 28.10.2004, 00:00 authored by Abdelhafid Benksim, Daniel Beaupère, Anne Wadouachi
An efficient synthesis of 1,2-trans-glycosyl cyanides via 1,2-O-sulfinyl monosaccharides is described. Such SN2-type displacements at the anomeric center are stereospecific and are best performed with sodium cyanide in the presence of ytterbium triflate. Significantly, the resulting 1,2-trans-glycosyl cyanides have a free hydroxyl group at C-2 ready for further modification.