title: A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides.
abstract: [reaction: see text] A fluorine-labeled selenide linker for installing terminal isolated olefins has been synthesized in high overall yield. The resin-bound linker could be glycosylated both with glycosyl trichloroacetimidates and glycosyl fluorides. The linker did not decompose after oxidation with tBuOOH but underwent beta-elimination when it was subjected to heat. This allowed the released n-pentenyl glycoside 15 to be isolated in excellent yield and purity after filtration.
authors.affiliation: Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden.
authors.forename: Mickael
authors.initials: M
authors.lastname: Mogemark
authors.forename: Linda
authors.initials: L
authors.lastname: Gustafsson
authors.forename: Christoffer
authors.initials: C
authors.lastname: Bengtsson
authors.forename: Mikael
authors.initials: M
authors.lastname: Elofsson
authors.forename: Jan
authors.initials: J
authors.lastname: Kihlberg
mesh_terms: D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D018036:Selenium Compounds / Q000737:chemistry*
chemical_list: D005960:Glucosides; D006845:Hydrocarbons, Fluorinated; D018036:Selenium Compounds