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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

*  and
Department of Chemistry, Tamkang University, No151 Yingzhuan Rd, 25137 Tamsui Dist., New Taipei City, Taiwan
* Author to whom correspondence should be addressed.
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 (CC BY 3.0).
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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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