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

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-glycos...

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Bibliographic Details
Published in:Organic letters 2004-10, Vol.6 (22), p.3913-3915
Main Authors: Benksim, Abdelhafid, Beaupère, Daniel, Wadouachi, Anne
Format: Article
Language:English
Subjects:
Cyanides - chemical synthesis
Cyanides - pharmacology
Glycosides - chemical synthesis
Glycosides - pharmacology
Glycosylation
Hydroxides - chemistry
Molecular Structure
Monosaccharides - chemistry
Stereoisomerism
Sulfinic Acids - chemistry
Ytterbium - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0486829