Glucose phenylosazone preparation

D-Glucosone (XII), prepared from D-glucose phenylosazone (XI) by the action of concentrated hydrochloric acid, is treated in aqueous solution with potassium cyanide. The imino-D-glucoascorbic acid (XIV) which readily separates shows many of the properties of ascorbic acid. Thus it shows a strong selective absorption band in the ultra-... 

The formation of D-glucose phenylosazone from chitosamine showed its relationship to D-glucose and D-mannose and Irvine and Hynd7 succeeded in preparing both D-mannose and D-glucose from chitosamine. 

Partially methylated derivatives of D-glucosone have been prepared by decomposition of the corresponding partially methylated phenylosazones with p-nitrobenzaldehyde osones have been obtained from 5-0-methyl-D-glucose phenylosazone and from 3,4,5-tri-O-methyl-D-glucose phenylosazone in this way.22 Although 6-0-methyl-D-glucose phenylosazone is not altered by heating with benzaldehyde or piperonal in aqueous ethanolic... 

It has recently been reported21 that a mixed osazone of 3,4-di-O-methyl-D-glucose can be converted, by treatment with p-nitrobenzaldehyde, into an osone which reacts with phenylhydrazine to give 3,4-di-O-methyl-D-glucose phenylosazone. Von Lebedev29 claimed to have obtained D-glu-cosone 6-phosphate, isolated as an amorphous lead salt, by the action of hydrochloric acid on the phenylosazone prepared from D-fructose 6-phosphate. 

Bayne, Fewster and Mitchell16 prepared VII by the method of Stacey and Turton, and recorded physical properties closely agreeing with those reported by Maurer.66 The compound was clearly related to D-glucosone, prepared from D-glucose phenylosazone and by direct oxidation, since, on treatment with dry acetone containing concentrated sulfuric acid, it gave crystalline tri-0-isopropylidene-(2-hydroxy-D-arabmo-hexose). 7... 

Again no free primary alcohol residue could be detected in the phenylosazone prepared directly from 3,6-anhydro-D-glucose, no reaction taking place with triphenylmethyl chloride or even with p-toluenesulfonyl... 

This compound was isolated by Diels and Meyer " on boiling o-glucose phenylosazone in methanol containing traces of sulfuric acid. They believed it to be identical with 3,6-anhydro- o-glucose phenylosazone, which had previously been prepared by other means." After observing differences in the physical properties of the two compounds, they suggested formula XVII, which they modified a year later " by proposing the pyrazole structure XVIII. This was found to be inadequate for several reasons, and the bicyclic formula XIX, or XX, was put forward by Percival." ... 

This osone was first prepared from cellobiose phenylosazone by the benzaldehyde method196 on hydrolysis by emulsin it gave D-glucosone and D-glucose. 

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