Electrochemical behaviour of new electroreducible amphiphilic saccharide derivatives II: Electroreduction in protic media

Maurice, Catherine; Schöllhorn, Bernd; Aboab, Bettina; Mousset, G.; Mousty, Christine

doi:10.1039/a906282c

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2000

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“…Further investigations, especially electrolyses in an aqueous medium of these ketones, are in progress in our group. [22] …”

Section: Resultsmentioning

confidence: 97%

Electrochemical Reduction in an Aprotic Medium of New Functionalized Amphiphilic Molecules Derived from Sugars: Stereoselective Pinacolization and an Example of a Glycosidic Carbon-Oxygen Bond Cleavage

Maurice¹,

Schöllhorn²,

Canet³

et al. 2000

Eur. J. Org. Chem.

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Electroreducible amphiphilic aromatic ketones derived from D‐glucose and D‐glucofuranurono‐6,3‐lactone (D‐glucurone) have been synthesized by Schmidt condensation and reaction of the unprotected lactone with the appropriate substrates, respectively. The macroscale electrolyses of the glucose derivatives, performed in an aprotic solvent (DMF), yield the pinacols possessing two glycosidic side chains. Under the same conditions of electrolysis with the D‐glucurone derivative, the glyosidic carbon‐oxygen bond is cleaved. The use of a redox mediator (couple anthracene−•/anthracene) has demonstrated that a glucosidic bond can be reduced by a homogeneous electron transfer. In the presence of a proton donor the expected D‐glucuronic pinacol is obtained. The radical‐radical coupling involves the formation of two chiral centers. The diastereo‐ and the enantioselectivity of the reaction have been studied by 1H‐ and 2H‐NMR spectroscopy, respectively.

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“…Further investigations, especially electrolyses in an aqueous medium of these ketones, are in progress in our group. [22] …”

Section: Resultsmentioning

confidence: 97%

Electrochemical Reduction in an Aprotic Medium of New Functionalized Amphiphilic Molecules Derived from Sugars: Stereoselective Pinacolization and an Example of a Glycosidic Carbon-Oxygen Bond Cleavage

Maurice¹,

Schöllhorn²,

Canet³

et al. 2000

Eur. J. Org. Chem.

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Electrochemical behaviour of new electroreducible amphiphilic saccharide derivatives II: Electroreduction in protic media

Abstract: L aboratoire de Etude de Biologique Synthe`se, Electrosynthe`se, Syste`mes a`Inte reü t (CNRS UMR 6504) a Equipe et Electroanalyse Bioorganique and dÏElectrosynthe`se

Cited by 1 publication

References 7 publications

Electrochemical Reduction in an Aprotic Medium of New Functionalized Amphiphilic Molecules Derived from Sugars: Stereoselective Pinacolization and an Example of a Glycosidic Carbon-Oxygen Bond Cleavage

Electrochemical Reduction in an Aprotic Medium of New Functionalized Amphiphilic Molecules Derived from Sugars: Stereoselective Pinacolization and an Example of a Glycosidic Carbon-Oxygen Bond Cleavage

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