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Gram‐scale synthesis and efficient purification of 13 C‐labeled levoglucosan from 13 C glucose
Author(s) -
Alexander Lisa,
Hoyt Caroline,
Michalczyk Ryszard,
Wu Ruilian,
Thorn Dave L.,
Silks L. A. ‘Pete’
Publication year - 2013
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2978
Subject(s) - levoglucosan , chemistry , yield (engineering) , anomer , gram , chromatography , chemical synthesis , organic chemistry , biochemistry , bacteria , materials science , aerosol , biology , biomass burning , metallurgy , in vitro , genetics
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.