title: Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).
abstract: [Structure: see text] Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. pwipf@pitt.edu
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
authors.forename: Joshua G
authors.initials: JG
authors.lastname: Pierce
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000276:Adjuvants, Immunologic; D005699:Galactosylceramides; D006027:Glycosides; D007097:Imines; C103873:KRN 7000