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. © 2011.