title: A novel stereospecific synthesis of glycosyl cyanides from 1,2-O-sulfinyl derivatives.
abstract: [reaction: see text] An efficient synthesis of 1,2-trans-glycosyl cyanides via 1,2-O-sulfinyl monosaccharides is described. Such S(N)2-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.
authors.affiliation: Laboratoire des Glucides, FRE 2779 Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens, France.
authors.forename: Abdelhafid
authors.initials: A
authors.lastname: Benksim
authors.forename: Daniel
authors.initials: D
authors.lastname: Beaupère
authors.forename: Anne
authors.initials: A
authors.lastname: Wadouachi
mesh_terms: D003486:Cyanides / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006031:Glycosylation; D006878:Hydroxides / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D015018:Ytterbium / Q000737:chemistry
chemical_list: D003486:Cyanides; D006027:Glycosides; D006878:Hydroxides; D009005:Monosaccharides; D013441:Sulfinic Acids; D015018:Ytterbium