Saccharinic acids phenylhydrazide

The saccharinic acids formed from some of the pentoses and hexoses have been the objects of study by Nef and his students. Glattfeld and Hanke reported in 1918 that, during the oxidation of maltose in alkaline solution, an acid had been produced whose phenylhydrazide had an analysis agreeing perfectly with that calculated for a four-carbon saccharinic acid. Furthermore, the properties of the free aeid were those which would be expected of one of these acids. Its configuration could not, however, be reported at that time because of the absence of data as to the properties and constants of the four-carbon saccharinic acids. Nef had also referred to the handicap which this lack of information had imposed on the work with sugars in alkaline solution. Consequently, with this in mind, Glattfeld began in 1920 the systematic synthesis of the four-carbon saccharinic acids. 

With sufficient quantities of the dl saccharinic acid thus available, many salts, as well as the crystalline phenylhydrazide, were prepared. All attempts at the resolution of this racemic acid by means of strychnine, quinine, or brucine failed to give, on hydrolysis of the alkaloid salts, an optically active acid. However, Glattfeld and Sherman were inclined to beheve that resolution had actually been accomplished by means of... 

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