title: Synthesis of methyl alpha-L-vancosaminide.
abstract: The synthesis of methyl alpha-L-vancosaminide from di-O-acetyl-L-rhamnal is described. The allylic alcohol methyl 2,3,6-trideoxy-3-C-methyl-alpha-L-threo-hex-2-enopyranoside was prepared from the glycal, 1,5-anhydro-1,2,6-trideoxy-3-C-methyl-L-ribo-hex-1-enitol, and converted to its N,N-dimethylisourea derivative. The cis amino alcohol functionality in vancosamine was introduced by the electrophilic cyclization of the isourea, followed by hydrolysis of the resulting oxazoline.
authors.affiliation: Department of Chemistry, Villanova University, PA 19085, USA.
authors.forename: G R
authors.initials: GR
authors.lastname: Smith
authors.forename: R M
authors.initials: RM
authors.lastname: Giuliano
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis*; D006595:Hexosamines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy
chemical_list: D000606:Amino Sugars; D006595:Hexosamines; C410154:methyl vancosaminide; C001946:vancosamine