title: Convenient synthesis of 3,4-dichloro-5-hydroxy-2(5H)-furanone glycoconjugates.
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.
authors.affiliation: Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors.forename: Edyta
authors.initials: E
authors.lastname: Gondela
authors.forename: Krzysztof Z
authors.initials: KZ
authors.lastname: Walczak
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D005663:Furans; D006001:Glycoconjugates; C067157:3,4-(dichloro)-5-hydroxy-2(5H)-furanone