title: Preparation of L-vancosamine-related glycosyl donors.
abstract: An improved practical synthesis of L-vancosamine-related glycosyl donors is described. The key steps include (1) stereoselective addition of methylcerium reagent to oximino ether and (2) stereoselective hydrogenation of exocyclic unsaturated glycoside in the presence of Wilkinson catalyst with C(5) inversion to give L-vancosamine derivatives. Three glycosyl donors were prepared, and their reactivities in the aryl C-glycoside formation were compared. Conversion of primary amine and azide to the corresponding N,N-dimethyl derivative is also described.
authors: Department of Chemistry, Tokyo Institute of Technology, Tokyo, Japan.
authors: Kei
authors: K
authors: Kitamura
authors: Masayuki
authors: M
authors: Shigeta
authors: Yoshihiko
authors: Y
authors: Maezawa
authors: Yukie
authors: Y
authors: Watanabe
authors: Day-Shin
authors: DS
authors: Hsu
authors: Yoshio
authors: Y
authors: Ando
authors: Takashi
authors: T
authors: Matsumoto
authors: Keisuke
authors: K
authors: Suzuki
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D006027:Glycosides; D006595:Hexosamines; C001946:vancosamine