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

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

Edyta Gondelaemail and Krzysztof Z. Walczak* email
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; in revised form: 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

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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.

AMA Style

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

Chicago/Turabian Style

Gondela, Edyta; Walczak, Krzysztof Z. 2011. "Convenient Synthesis of 3,4-Dichloro-5-hydroxy-2(5H)-Furanone Glycoconjugates." Molecules 16, no. 2: 1011-1020.

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