Alduronic acids, oxidation

The oxidation of D-glucose 1-phosphate and analogues to the alduronic acid 1-phosphates by molecular oxygen over Pt on carbon occurred with... 

Treatment of the alduronic acid 180 with DAIB-I2 furnishes the formyloxylactone 182 (Scheme 52) (98JOC2099). This and related reactions proceed by a radical fragmentation-oxidation sequence, culminating in the formation and intramolecular capture of oxycarbenium ion intermediates (e.g., 181). 

The synthesis of glycosiduronic acids includes two main approaches one involves selective oxidation of the primary hydroxyl group of a neutral glycoside, and the other, condensation of the agly-con with an appropriately protected alduronic acid derivative. The present Section is concerned mainly with the synthetic methods leading to glycosiduronic acids. An attempt has been made to collate information on the reactions of glycosiduronic acids, and to illustrate some of the physical methods that have contributed to the characterization of these compounds. 

H. S. Isbell, H. L. Frush, and Z. Orhanovic, Oxidation of sodium salts of alduronic and glyculosonic acids by sodium peroxide, Carbohydr. Res., 36 (1974) 283-291 Oxidation of certain cyclic carbonyl compounds with alkaline hydrogen peroxide, ibid., 43 (1975) 93-100 H. S. Isbell, Concurrent oxidation and reduction reactions of cyclohexanehexone, rhodizonic acid, and tetrahydroxy-l,4-benzoquinone with hydrogen peroxide, ibid., 39 (1975) C4-C7. 

Isbell, H. S., H. L. Frush, and Z. Orhanovic Reaction of Carbohydrates with Hydroperoxides III. Oxidation of Sodium Salts of Alduronic and Glyulosonic Acids by Sodium Peroxide. Carbohydrate Res. 36, 283 (1974). 

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