C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction

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Abstract

Palladium-catalyzed oxidation can single out the secondary hydroxyl group at C3 in glucose, circumventing the more readily accessible hydroxyl at C6 and the more reactive anomeric hydroxyl. Oxidation followed by reduction results in either allose or allitol, each a rare sugar that is important in biotechnology. Also, N-acetylglucosamine is selectively oxidized at C3. These results demonstrate that glucose and N-acetylglucosamine, the most readily available chiral building blocks, can be versatile substrates in homogeneous catalysis.

Original languageEnglish
Pages (from-to)11439-11443
Number of pages5
JournalJournal of Organic Chemistry
Volume81
Issue number22
DOIs
Publication statusPublished - 18-Nov-2016

Keywords

  • SELECTIVE CATALYTIC-OXIDATION
  • OXO-SUGARS
  • LIQUID-CHROMATOGRAPHY
  • PYRIDINE SOLUTION
  • ACID DERIVATIVES
  • AQUEOUS-SOLUTION
  • D-FRUCTOSE
  • CHEMISTRY
  • WATER
  • MONOSACCHARIDES

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