Orthosaccharinic acids

Conversion to 2-Desoxyaldonic Adds.—The dihalides of the glycals, as well as the corresponding 2-desoxy-2-halogeno-aldoses, can be isomer-ized into the 2-desoxyaldonic acids (orthosaccharinic acids) by treatment with lead oxide in water. 

A review (in Russian) has been published by Gakhokidze, and the same author has reported on the conversion of 3,4,6-tri-O-acetyl-D-mannose into 2-deoxy-D-araZ>mo-hexonic acid(orthosaccharinic acid) by use of aqueous lead hydroxide. The first naturally occurring branched-chain saccharinic acid, 2-C-methyl-D-erythronolactone, has been isolated from milk vetch Astragalus lusitanicus) Reduction of the isosaccharinic acids (13) and (14) with sodium borohydride gave mixtures of the corresponding free sugars and branched-chain alditols. ... 

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