title: C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.
abstract: The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.
authors.affiliation: Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10065, USA; The Graduate Center, CUNY, 365 5th Avenue, New York, NY 10016, USA.
authors.forename: Ahmad S
authors.initials: AS
authors.lastname: Altiti
authors.affiliation: Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10065, USA; The Graduate Center, CUNY, 365 5th Avenue, New York, NY 10016, USA. Electronic address: dmootoo@hunter.cuny.edu.
authors.forename: David R
authors.initials: DR
authors.lastname: Mootoo
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D062845:Chloroacetates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005699:Galactosylceramides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D062845:Chloroacetates; D005699:Galactosylceramides; C009528:trichloroacetamide; C103873:KRN 7000
keywords: C-Glycoside; Glycolipid; Glycomimetic; Imidate; Iodocyclization; KRN7000; Oxazine