A Disaccharide Rearrangement Catalyzed by Molybdate Anion in Aqueous Solution

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• 作者：Qingquan Wu ; Qingfeng Pan ; Shikai Zhao ; Heidi Imker ; Anthony S. Serianni
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：April 13, 2007
• 年：2007
• 卷：72
• 期：8
• 页码：3081 - 3084
• 全文大小：89K
• 年卷期：v.72,no.8(April 13, 2007)
• ISSN：1520-6904

文摘

Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueoussolution at 67 C gave an equililibrium mixture containingthe reactant aldofuranose (42%) and a 2-ketopentofuranosegalactosylated at O1 (58%). Observation of this stereospecificrearrangement supports prior arguments that substituents atC2 of the branched-chain aldofuranose reactant are locatedin a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. Thisrearrangement provides a new and convenient route to2-ketosugars glycosylated at the exocyclic C1 position.