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.
[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.
Schweizer
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The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan. frank.schweizer@ualberta.ca
Inazu
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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
D000085:Acetates; D002241:Carbohydrates; D004852:Epoxy Compounds; D006027:Glycosides; D007783:Lactones; C016274:bromoacetate