title: Use of phenyl 2-alpha-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions.
abstract: Phenyl 2-alpha-selenoglycosides of Neu5Ac were successfully prepared from the corresponding peracetylated chloro derivative of Neu5Ac 1 and phenylselenol in the presence of N,N-di-isopropylethylamine in excellent yields. The reaction of with various alcohols was effectively catalyzed by NIS/TfOH or DMTST to produce a variety of glycosides in moderate yields. Selective activation of over phenyl 2-alpha-thioglycoside of Neu5Ac with AgOTf/K(2)CO(3) was also achieved.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan. ikeda@ys2.u-shizuoka-ken.ac.jp
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Ikeda
authors.forename: Yuji
authors.initials: Y
authors.lastname: Sugiyama
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tanaka
authors.forename: Masayuki
authors.initials: M
authors.lastname: Sato
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis; D006031:Glycosylation; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives*; D018036:Selenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D018036:Selenium Compounds; D019158:N-Acetylneuraminic Acid