title: Syntheses of carbocyclic analogues of α-D-glucosamine, α-D-mannose, α-D-mannuronic acid, β-L-idosamine, and β-L-gulose.
abstract: A versatile synthesis of orthogonally protected derivatives of carba-α-D-glucosamine, carba-α-D-mannose, carba-α-D-mannuronic acid, carba-β-L-idosamine, and carba-β-L-gulose from methyl α-D-mannoside is described. Our synthetic strategy utilizes the palladium-promoted Ferrier carbocyclization and persistent butane-2,3-diacetal protection to produce a key chiral cyclohexanone intermediate, from which all five carbasugar derivatives can readily be obtained.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, Canada M5S 3H6.
authors.forename: Yunshan
authors.initials: Y
authors.lastname: Sun
authors.forename: Mark
authors.initials: M
authors.lastname: Nitz
mesh_terms: D002236:Carbohydrate Conformation; D005944:Glucosamine / Q000138:chemical synthesis* / Q000737:chemistry; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D006603:Hexuronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006601:Hexoses; D006603:Hexuronic Acids; C057406:gulose; C008324:mannuronic acid; D005944:Glucosamine; D008358:Mannose