title: Improved and large-scale synthesis of certain glycosyl cyanides. Synthesis of 2,5-anhydro-5-thio-D-allononitrile.
abstract: The first synthesis of 2,5-anhydro-5-thio-D-allononitrile starting with L-lyxose, via a trifluoromethanesulfonic ester intermediate, has been accomplished. Methods have been developed to achieve a large-scale synthesis of 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-talo-heptononitrile (5). An improved procedure has been developed to synthesize 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulononitrile (9). The structures of 5 and the thioamide derivative from 9, 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulonothioamide, were confirmed by X-ray crystallographic analysis.
mesh_terms: D002236:Carbohydrate Conformation; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009570:Nitriles / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
chemical_list: D007202:Indicators and Reagents; D009570:Nitriles; C052126:2,5-anhydro-5-thionitrile