title: A general synthesis of iminosugars.
abstract: 1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.
authors.affiliation: Centre for Synthesis and Chemical Biology, Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Ciaran
authors.initials: C
authors.lastname: McDonnell
authors.forename: Linda
authors.initials: L
authors.lastname: Cronin
authors.forename: Julie L
authors.initials: JL
authors.lastname: O'Brien
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D017485:1-Deoxynojirimycin / Q000138:chemical synthesis; D019380:Anti-HIV Agents / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis*; D005688:Galactosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007097:Imines / Q000138:chemical synthesis*
chemical_list: D019380:Anti-HIV Agents; D002241:Carbohydrates; D007097:Imines; D017485:1-Deoxynojirimycin; D005688:Galactosamine