title: Efficient synthesis of an alpha(2,9) trisialic acid by one-pot glycosylation and polymer-assisted deprotection.
abstract: An efficient synthesis of alpha(2,9) trisialic acid has been achieved via one-pot glycosylation and polymer-assisted deprotection. The synthesis involves chemo- and regioselective alpha-sialylation of ethylthiosialoside with the S-benzoxazolyl (S-Box) sialyl donor. Use of a prelinker to link an activated ester and a vinyl ether via a carbon chain enables polymer-assisted deprotection of the protected trisialic acids.
authors.affiliation: Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo 152-8552, Japan. thiroshi@apc.titech.ac.jp
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tanaka
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Tateno
authors.forename: Yuji
authors.initials: Y
authors.lastname: Nishiura
authors.forename: Takashi
authors.initials: T
authors.lastname: Takahashi
mesh_terms: D006031:Glycosylation; D011108:Polymers / Q000737:chemistry; D012794:Sialic Acids / Q000138:chemical synthesis*
chemical_list: D011108:Polymers; D012794:Sialic Acids; C543094:alpha(2,9) trisialic acid