title: Access to 3-O-Functionalized N-Acetylneuraminic Acid Scaffolds.
abstract: Direct access to 3-O-functionalized 2-α-N-acetylneuraminides and their corresponding 2,3-dehydro-2-deoxy-N-acetylneuraminic acid derivatives is described. Initially, a stereoselective ring-opening of the key intermediate N-acetylneuraminic acid (Neu5Ac) 2,3-β-epoxide with an alcohol provided the 3-hydroxy α-glycoside. O-Alkylation of the C3 hydroxyl group generated novel 3-O-functionalized Neu5Ac derivatives that provided the corresponding unsaturated derivatives upon elimination.
authors.affiliation: Institute for Glycomics, Griffith University - Gold Coast Campus, Queensland 4222, Australia.
authors.forename: Mauro
authors.initials: M
authors.lastname: Pascolutti
authors.affiliation: Institute for Glycomics, Griffith University - Gold Coast Campus, Queensland 4222, Australia.
authors.forename: Paul D
authors.initials: PD
authors.lastname: Madge
authors.affiliation: Institute for Glycomics, Griffith University - Gold Coast Campus, Queensland 4222, Australia.
authors.forename: Robin J
authors.initials: RJ
authors.lastname: Thomson
authors.affiliation: Institute for Glycomics, Griffith University - Gold Coast Campus, Queensland 4222, Australia.
authors.forename: Mark
authors.initials: M
authors.lastname: von Itzstein
mesh_terms: D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D006027:Glycosides; D012794:Sialic Acids; C036137:2-deoxy-2,3-dehydro-N-acetylneuraminic acid; D019158:N-Acetylneuraminic Acid