title: Gram-scale synthesis and efficient purification of 13C-labeled levoglucosan from 13C glucose.
abstract: (13)C-Labeled levoglucosan has been synthesized and purified in good yield, and on the gram scale in one step from commercially available (13)C glucose. This one-step protocol uses 2-chloro-1,3-dimethylimidazolinium chloride that serves to selectively activate the anomeric carbon toward substitution reactions. The labeled glucose is then smoothly converted to the anhydroglucose. Purification is efficiently achieved on large scale by chromatography on silica gel.
authors.affiliation: Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, MS E529, Los Alamos, NM, 87544, USA.
authors.forename: Lisa
authors.initials: L
authors.lastname: Alexander
authors.forename: Caroline
authors.initials: C
authors.lastname: Hoyt
authors.forename: Ryszard
authors.initials: R
authors.lastname: Michalczyk
authors.forename: Ruilian
authors.initials: R
authors.lastname: Wu
authors.forename: Dave L
authors.initials: DL
authors.lastname: Thorn
authors.forename: L A Pete
authors.initials: LA
authors.lastname: Silks
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification
chemical_list: D002247:Carbon Isotopes; C014989:1,6-anhydro-beta-glucopyranose; D005947:Glucose
keywords: 1,6-anhydroglucose; carbon-13 labeled; large scale; levoglucosan