Carbohydrate research

Chromic acid oxidation in the synthesis of uronic acids. Use of the O-levulinoyl group to minimize acyl migration

RN Rej, JN Glushka, W Chew, AS Perlin

Index: Rej, Rabindra N.; Glushka, John N.; Chew, Warren; Perlin, Arthur S. Carbohydrate Research, 1989 ,  vol. 189, p. 135 - 148

Full Text: HTML

Citation Number: 16

Abstract

Abstract In the chromate oxidation of a partially acylated sugar derivative to form the corresponding uronic acid, acyl migration to the primary alcohol group is a frequent cause of interference. In contrast to more commonly employed ester substituents, the O-levulinoyl group is far less prone to migration during oxidations with Jones reagent (chromic-sulfuric acids). Examples described here include levulinoyl at O-5 of acylic and furanose ...