Gram-scale synthesis and efficient purification of 13C-labeled levoglucosan from 13C glucose§

Authors

  • Lisa Alexander,

    1. Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, Los Alamos, NM, USA
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    • LANL summer undergraduate student. Currently at UC Berkeley, Department of Chemistry (8/12).

  • Caroline Hoyt,

    1. Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, Los Alamos, NM, USA
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    • LANL graduate student. Currently at Georgia Institute of Technology, Department of Chemistry (8/12).

  • Ryszard Michalczyk,

    1. Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, Los Alamos, NM, USA
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  • Ruilian Wu,

    1. Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, Los Alamos, NM, USA
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  • Dave L. Thorn,

    1. Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, Los Alamos, NM, USA
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  • L. A. ‘Pete’ Silks

    Corresponding author
    • Bioscience Division, Bioenergy and Environmental Science Group B-8, Los Alamos National Laboratory, Los Alamos, NM, USA
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  • §

    Additional Supporting Information may be found in the on-line version of this article.

Correspondence to: L. A. ‘Pete‘ Silks, Bioscience Division, Bioenergy and Environmental Science Group B-8, MS E529, Los Alamos, NM 87544, USA.

E-mail: pete-silks@lanl.gov

Abstract

13C-Labeled levoglucosan has been synthesized and purified in good yield, and on the gram scale in one step from commercially available 13C 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.

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