title: Stereoselective synthesis of S-linked α(2→8) and α(2→8)/α(2→9) hexasialic acids.
abstract: A new approach for the synthesis of S-linked α(2→8) and alternating α(2→8)/α(2→9) oligosialic acids by S-alkylation has been developed, using chemo- and stereoselective alkylation of a C2-thiolated sialoside donor (nucleophile) with either a C8- or C9-iodide-activated sialoside acceptor (electrophile). An efficient intramolecular acetyl group migration from the C7 to C9-position of the sialoside under mild basic conditions was used to generate the C8-iodide, the key sialyl acceptor (electrophile). Using this strategy, the syntheses of S-linked α(2→8) and α(2→8)/α(2→9) hexasialic acids were achieved.
authors.affiliation: Department of Chemistry, National Tsing Hua University, 101 Section 2, Kuang Fu Road, Hsinchu 30013, Taiwan.
authors.forename: Chien-Fu
authors.initials: CF
authors.lastname: Liang
authors.forename: Ting-Chun
authors.initials: TC
authors.lastname: Kuan
authors.forename: Tsung-Che
authors.initials: TC
authors.lastname: Chang
authors.forename: Chun-Cheng
authors.initials: CC
authors.lastname: Lin
mesh_terms: D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012794:Sialic Acids