title: Intramolecular nitrogen delivery for the synthesis of C-glycosphingolipids. Application to the C-glycoside of the immunostimulant KRN7000.
abstract: The key reaction in this approach to C-glycosphingolipids is the stereoselective iodocyclization of a sugar-linked homoallylic carbonimidothioate. E and Z reaction substrates were assembled in a convergent fashion via an alkene metathesis strategy and exhibited the same alkene facial selectivity in the iodocyclization irrespective of alkene geometry, although the E alkene was found to be less reactive.
authors.affiliation: Department of Chemistry, Hunter College, City University of New York , New York, New York 10065, United States.
authors.forename: Ahmad S
authors.initials: AS
authors.lastname: Altiti
authors.forename: David R
authors.initials: DR
authors.lastname: Mootoo
mesh_terms: D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000276:Adjuvants, Immunologic; D000475:Alkenes; D005699:Galactosylceramides; D006028:Glycosphingolipids; D009584:Nitrogen; C103873:KRN 7000