A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution

Qingquan Wu; Qingfeng Pan; Shikai Zhao; Heidi Imker; Anthony S. Serianni

doi:10.1021/jo062494+

A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution

Qingquan Wu, Qingfeng Pan, Shikai Zhao, Heidi Imker, Anthony S. Serianni

Research output: Contribution to journal › Article › peer-review

Abstract

(Chemical Equation Presented) Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67°C gave an equilibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.

Original language	English (US)
Pages (from-to)	3081-3084
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	8
DOIs	https://doi.org/10.1021/jo062494+
State	Published - Apr 13 2007
Externally published	Yes

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Organic Chemistry

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10.1021/jo062494+

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title = "A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution",

abstract = "(Chemical Equation Presented) Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67°C gave an equilibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.",

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year = "2007",

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language = "English (US)",

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T1 - A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution

AU - Wu, Qingquan

AU - Pan, Qingfeng

AU - Zhao, Shikai

AU - Imker, Heidi

AU - Serianni, Anthony S.

PY - 2007/4/13

Y1 - 2007/4/13

N2 - (Chemical Equation Presented) Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67°C gave an equilibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.

AB - (Chemical Equation Presented) Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67°C gave an equilibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.

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A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution

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