title: Synthesis and x-ray crystallographic analysis of 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hexopyranosyl cyanide.
abstract: The glycopyranosyl cyanide 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hexopyranosyl cyanide has been synthesized from tri-O-acetyl-D-galactal by reaction with trimethylsilyl cyanide in the presence of boron trifluoride diethyl etherate followed by catalytic hydrogenation. The synthesis provides the α-anomer stereoselectively, the structure of which was assigned based on 2D NMR techniques and x-ray crystallography.
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA.
authors.forename: Madeline
authors.initials: M
authors.lastname: Rotella
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA.
authors.forename: Matthew
authors.initials: M
authors.lastname: Giovine
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA.
authors.forename: William
authors.initials: W
authors.lastname: Dougherty
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA.
authors.forename: Walter
authors.initials: W
authors.lastname: Boyko
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA.
authors.forename: Scott
authors.initials: S
authors.lastname: Kassel
authors.affiliation: Department of Chemistry, Villanova University, Villanova, PA 19085, USA. Electronic address: robert.giuliano@villanova.edu.
authors.forename: Robert
authors.initials: R
authors.lastname: Giuliano
mesh_terms: D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D003486:Cyanides / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D003486:Cyanides; D006601:Hexoses; D009570:Nitriles; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide
keywords: Glycopyranosyl cyanide