Journal
TETRAHEDRON-ASYMMETRY
Volume 21, Issue 18, Pages 2238-2243Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2010.07.027
Keywords
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Funding
- VEGA [2/0108/08]
- SP [2003SP200280203]
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A branched-chain aldose bearing an azido group at the C-2 position provides access to the corresponding 1-deoxy-1-azido- and 1-deoxy-1-amino ketoses in a single step via stereospecific isomerization. The isomerization exploited the catalytic effect of molybdate ions and microwave irradiation. The structures of the products were analyzed by NMR spectroscopy, IR, HRMS spectrometry and quantum-chemical DFT calculations. DFT-computed proton-proton coupling constants of the prepared Amadori ketose 1-deoxy1-amino-D-gluco-heptulose were found to be comparable with the experimentally obtained coupling constants and were in agreement with the C-4(1) pyranose form in aqueous solution at room temperature. (C) 2010 Elsevier Ltd. All rights reserved.
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