title: Synthesis of cholesteryl-α-D-lactoside via generation and trapping of a stable β-lactosyl iodide.
abstract: The generation of β-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available β-per-O-acetylated lactose with trimethylsilyl iodide (TMSI). The β-iodide was surprisingly stable as evidenced by NMR spectroscopy. Introduction of octanol or cholesterol under microwave conditions gave high yields of α-linked glycoconjugates. Careful analysis of the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides α-linked glycosylation products with a free C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling of immune modulating bacterial derived-glycans.
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, United States.
authors.forename: Ryan A
authors.initials: RA
authors.lastname: Davis
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, United States.
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, United States.
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
keywords: 1,2-cis; Glycosyl iodide glycosylation; H. pylori; Mechanism