Erythrose phenylosazone

The tetrosones have not been prepared. Fischer2 observed that erythrose phenylosazone is relatively resistant to concentrated hydrochloric acid on warming, some decomposition took place, but osone was not formed. 

Diels and Stephan173 treated the benzoate of 3-hydroxy-2-butanone with bromine, and obtained crystalline 1-bromo- and 1,1-dibromo- derivatives. With dilute alkali, these formed 4-deoxy-DL-gZycero-tetrulose and 4-deoxy-DL-erythrosone respectively. Both compounds gave with phenylhydrazine 4-deoxy-DL-erythrose phenylosazone, which had previously been prepared from the corresponding aldotetrose.174... 

Phenylosazone C14HMN402, dec 164-165°. Identical with D-erythrose phenylosazone. 

Same as D-erythrose phenylosazone. Same as D-lyxose phenylosazone. Same as D-talose phenylosazone. 

Deulofeu also degraded tetraacetyl-D-arabononitrile with sodium methoxide or by hydrolysis of the acetyl groups with sulfuric acid and separation of the nitrile group with silver carbonate. D-Erythrose was characterized as the phenylosazone. 

Ruff noticed in the mother liquors of an erythrose preparation obtained by degradation of L-arabonic acid, a small amount of another sugar, apparently a keto tetrose, which was not oxidized by bromine. The ketose gave the same phenylosazone as that obtained from L-ery-throse, but was not isolated otherwise. Neuberg oxidized erythritol to form an optically inactive tetrose solution and claimed that color reactions showed the presence of a keto tetrose. 

Repetition of this procedure on the galactosyl-arabinose gave O-jS-n-galacto-pyranosyl-D-erythrose (6) which did not give a phenylosazone. Hence, it was suggested that a 3-d-(1 4)-linkage is present in lactose (5). 

Keto-L-arabonic acid, prepared from the osone, loses carbon dioxide similarly, but the final product is not furfural but L-erythrose, isolated as the phenylosazone or as calcium L-erythronate after bromine oxidation ISl),... 

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