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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
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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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Abstract

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 3.0).

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MDPI and ACS Style

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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