title: Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold.
abstract: All stereoisomers of a highly functionalized 2,3-unsaturated C-glycoside can be accessed in 10-100 g quantities from readily available starting materials and reagents in 3-7 steps. These chiral scaffolds contain three stereogenic centers along with orthogonally protected functional groups for downstream reactivity.
authors.affiliation: Chemical Biology Platform, The Broad Institute of MIT and Harvard, 7 Cambridge Center, Cambridge, Massachusetts 02142, USA.
authors.forename: Baudouin
authors.initials: B
authors.lastname: Gerard
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Marié
authors.forename: Bhaumik A
authors.initials: BA
authors.lastname: Pandya
authors.forename: Maurice D
authors.initials: MD
authors.lastname: Lee
authors.forename: Haibo
authors.initials: H
authors.lastname: Liu
authors.forename: Lisa A
authors.initials: LA
authors.lastname: Marcaurelle
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D007202:Indicators and Reagents