title: Chain extension of sugar delta-lactones with the enolate of tert-butyl bromoacetate and elaboration into functionalized C-ketosides, C-glycosides, and C-glucosyl glycines.
abstract: [structure: see text] We describe the synthesis of a series of exocyclic sugar epoxides 1 prepared in a one-step procedure from sugar delta-lactones with the enolate of tert-butyl bromoacetate. Ring opening of the sugar oxiranes provides C-ketosides while reduction affords functionalized C-glycosides bearing an alpha-hydroxy ester moiety. The alpha-hydroxy ester can be converted into C-glucosyl glycine analogues 2.
authors.affiliation: The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan. frank.schweizer@ualberta.ca
authors.forename: F
authors.initials: F
authors.lastname: Schweizer
authors.forename: T
authors.initials: T
authors.lastname: Inazu
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000085:Acetates; D002241:Carbohydrates; D004852:Epoxy Compounds; D006027:Glycosides; D007783:Lactones; C016274:bromoacetate