title: Unexpected anomeric selectivity of a 1-C-arylglycal donor in Kdo glycoside synthesis.
abstract: A novel class of 1-C-arylglycals was developed and subjected to N-iodosuccinimide-mediated glycosylations with alcohols. Unexpectedly, all reactions provided 2-iodo-β-D-ketopyranosides in high yields and excellent stereoselectivity. After removal of the 2-iodide by radical conditions, the aryl group was smoothly oxidized to provide the corresponding β-Kdo glycosides. A mechanism for the stereoselective formation of β-D-ketopyranosides was proposed, which was supported by evidence from X-ray crystallography.
authors.affiliation: Alberta Ingenuity Centre for Carbohydrate Science, Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta T3G 3M9, Canada.
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Qian
authors.forename: Jianhao
authors.initials: J
authors.lastname: Feng
authors.forename: Masood
authors.initials: M
authors.lastname: Parvez
authors.forename: Chang-Chun
authors.initials: CC
authors.lastname: Ling
mesh_terms: D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry*
chemical_list: D006027:Glycosides; D013388:Succinimides; C008155:N-iodosuccinimide