title: A 5-Ureido-Modified Sialyl Donor: A Tool for the Synthesis of α-Sialosides.
abstract: A novel method for the synthesis of α-sialosides using a newly developed 5-ureido-modified sialyl donor is reported. The donor was found to be useful for α-selective sialidation with various glycosyl acceptors, forming α(2,6)Glc, α(2,6)Gal, and α(2,3)Gal linkages in excellent yield and with stereoselectivity. Furthermore, α-sialoside was easily isolated from the reaction mixture by the 1,5-lactamization method under mild conditions. Successful application of the C5-ureido sialyl donor to the synthesis of a sialoside confirmed the usefulness of the present method.
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University , 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
authors.forename: Maiko
authors.initials: M
authors.lastname: Tanase
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University , 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Imamura
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University , 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.|Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University , Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Hiromune
authors.initials: H
authors.lastname: Ando
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University , 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.affiliation: Department of Applied Bioorganic Chemistry, Gifu University , 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan.|Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University , Yoshida Ushinomiya-cho, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
mesh_terms: D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D012794:Sialic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D012794:Sialic Acids; D014508:Urea