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Molecules 2011, 16(2), 1011-1020; doi:10.3390/molecules16021011

Convenient Synthesis of 3,4-Dichloro-5-hydroxy-2(5H)-Furanone Glycoconjugates

Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
* Author to whom correspondence should be addressed.
Received: 14 December 2010 / Revised: 8 January 2011 / Accepted: 21 January 2011 / Published: 25 January 2011
(This article belongs to the Special Issue Glycosides)
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3,4-Dichloro-5-hydroxy-2(5H)-furanone treated with methyl chloroformate in the presence of diisopropylethylamine (Hünig’s base) gave the corresponding carbonate. The labile methoxycarbonyloxy group smoothly undergoes substitution by amino alcohols. The obtained 5-(w-hydroxyalkylamino) mucochloric acid derivatives reacted with peracetylated glucals using triphenylphosphine hydrobromide as a catalyst to give the title muchloric acid glycoconjugates.
Keywords: 3,4-dichloromucochloric acid; amino alcohol; glucals; addition; glycoconjugate 3,4-dichloromucochloric acid; amino alcohol; glucals; addition; glycoconjugate
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Gondela, E.; Walczak, K.Z. Convenient Synthesis of 3,4-Dichloro-5-hydroxy-2(5H)-Furanone Glycoconjugates. Molecules 2011, 16, 1011-1020.

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