title: Syntheses of alpha- and beta-C-glucopyranosyl serines from a common intermediate.
abstract: A versatile synthesis leading to either C-linked alpha- or beta-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the alpha-linkage. A transposition of these last steps leads to the beta-linked isomer selectively.
authors.affiliation: Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York 13346, USA. enolen@colgate.edu
authors.forename: Ernest G
authors.initials: EG
authors.lastname: Nolen
authors.forename: Laurence A
authors.initials: LA
authors.lastname: Donahue
authors.forename: Rebecca
authors.initials: R
authors.lastname: Greaves
authors.forename: Trevor A
authors.initials: TA
authors.lastname: Daly
authors.forename: David R
authors.initials: DR
authors.lastname: Calabrese
mesh_terms: D003500:Cyclization; D004951:Esterification; D005947:Glucose / Q000737:chemistry*; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D012694:Serine; D005947:Glucose