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
✍ Scribed by Catherine Maurice; Bernd Schöllhorn; Isabelle Canet; Guy Mousset; Christine Mousty; Jérôme Guilbot; Daniel Plusquellec
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 461 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
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