Synthesis of Acids and Amino Acids by Selective Oxidation of Primary Hydroxyl Groups to Carboxylic acids in Sugars


  •  Natarajan Raju    
  •  Rolf E. Swenson    

Abstract

Preferential oxidation of primary hydroxyls in unprotected sugars and sugar amino acids is reported using inexpensive and readily available reagents. This method offers a specific oxidation protocol for a variety of carbohydrates. The stereochemical integrity of the starting materials was preserved and a simple workup yielded the products in good yields with high purity. The procedure is compatible with base sensitive groups like Fmoc.  Both mono and disaccharides undergo oxidation regioselectively.



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