title: Targeted glycosyl donor delivery for site-selective glycosylation.
abstract: [reaction: see text]n-Pentenyl ortho esters (NPOEs) and n-pentenyl glycosides (NPGs) are interconvertible glycosyl donors which are activated by reaction with halonium ions. In a series of cyclic syn-1,3-diols, NPOEs have been found to specifically glycosylate the equatorial-OH while the NPG glycosylates predominantly, but not exclusively, the axial-OH. When the cyclic diol acceptor is presented with equivalent amounts of an NPOE and an NPG in a three-component-reaction, a single, double-glycosylation product is obtained, which conforms to the foregoing preferences, presenting evidence for site-selective glycosylation.
authors.affiliation: Natural Products and Glycotechnology Research Institute, Inc., Durham, North Carolina 27707, USA.
authors.forename: G
authors.initials: G
authors.lastname: Anilkumar
authors.forename: L G
authors.initials: LG
authors.lastname: Nair
authors.forename: B
authors.initials: B
authors.lastname: Fraser-Reid
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data
chemical_list: D000475:Alkenes; D006027:Glycosides; D007202:Indicators and Reagents