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Molecules 2012, 17(4), 4498-4507; doi:10.3390/molecules17044498
Article

Regioselectivity in the Ring Opening of Epoxides for the Synthesis of Aminocyclitols from D-(-)-Quinic Acid

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Received: 26 March 2012 / Revised: 9 April 2012 / Accepted: 10 April 2012 / Published: 16 April 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

Efficient syntheses of four aminocyclitols are reported. Each synthesis is accomplished in eight steps starting from D-(-)-quinic acid. The key step involves a highly regioselective ring opening of epoxides by sodium azide.
Keywords: aminocyclitols; epoxides; glycosidase inhibitors; D-(-)-quinic acid; regioselective ring opening aminocyclitols; epoxides; glycosidase inhibitors; D-(-)-quinic acid; regioselective ring opening
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Shih, T.-L.; Yang, S.-Y. Regioselectivity in the Ring Opening of Epoxides for the Synthesis of Aminocyclitols from D-(-)-Quinic Acid. Molecules 2012, 17, 4498-4507.

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