title: Stereoselective glycosylation of exo-glycals accelerated by Ferrier-type rearrangement.
abstract: [reaction: see text] Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.
authors.affiliation: Institute of Biological Chemistry, Academia Sinica, No. 128, Academia Road Section 2, Nan-Kang, Taipei, 11529, Taiwan.
authors.forename: Hui-Chang
authors.initials: HC
authors.lastname: Lin
authors.forename: Wen-Bin
authors.initials: WB
authors.lastname: Yang
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Gu
authors.forename: Chen-Yin
authors.initials: CY
authors.lastname: Chen
authors.forename: Chung-Yi
authors.initials: CY
authors.lastname: Wu
authors.forename: Chun-Hung
authors.initials: CH
authors.lastname: Lin
mesh_terms: D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure
chemical_list: D006001:Glycoconjugates; D006027:Glycosides