title: Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of α-Se-GalCer.
abstract: The TiCl4 induced anomerization of selenium glycosides of galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid groups were attached to the anomeric Se atom. An increased amount of TiCl4 and/or higher temperature were needed to ensure completion of the reaction in some cases. Yields were higher for reactions carried out at higher dilution. The reaction was applied to the synthesis of Se-based mimics of the potent immunostimulant α-GalCer (KRN7000).
authors.affiliation: School of Chemistry, National University of Ireland Galway , University Road, Galway, Ireland.
authors.forename: Anthony W
authors.initials: AW
authors.lastname: McDonagh
authors.affiliation: Department of Chemistry, University of Bath , Claverton Down, Bath BA2 7AY, United Kingdom.
authors.forename: Mary F
authors.initials: MF
authors.lastname: Mahon
authors.affiliation: School of Chemistry, National University of Ireland Galway , University Road, Galway, Ireland.
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012643:Selenium / Q000737:chemistry*; D014025:Titanium
chemical_list: D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; D006027:Glycosides; D058116:Lewis Acids; D016566:Organoselenium Compounds; C000608390:alpha-Se-GalCer; C493154:alpha-galactosylceramide; C025096:titanium tetrachloride; D014025:Titanium; D012643:Selenium; C103873:KRN 7000