A novel stereospecific synthesis of glycosyl cyanides from 1,2-O-sulfinyl derivatives.
[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.
Benksim
Abdelhafid
A
Laboratoire des Glucides, FRE 2779 Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens, France.
Beaupère
Daniel
D
Wadouachi
Anne
A
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
D003486:Cyanides; D006027:Glycosides; D006878:Hydroxides; D009005:Monosaccharides; D013441:Sulfinic Acids; D015018:Ytterbium