D-Galactose oxime

A cyclic hexaacetyl oxime (XII) was also isolated by mild acetylation of D-galactose oxime and by treatment with sodium acetate and acetic anhydride. A cyclic aldoxime acetate (XIII) was also obtained by Voto6ek from D-fucose oxime, and by Restelli de Labriola and Deulofeu ... 

D-Galactose oxime, IV, 122, 124 —, hexaacetyl-, IV, 123, 160 D-Galactose phenylhydrazones, and their pentaacetates, III, 26 D-Galactose phenylosazone, III, 29, 34 D-Galactose phenylosazone anhydride, III, 31, 39... 

Conversion of the aldehyde into a nitrile is accomplished by treatment of an aldose with hydroxvlamine to give an oxime (Section 19.8), followed by dehydration of the oxJme with acetic anhydride. The Wohl degradation does not give particularly high yields of chain-shortened aldoses, but the reaction is general for all aldopentoses and aldohexoses. For example, D-galactose is converted by Wohl degradation into n-lyxose. 

The first benzoylated nitrile of an aldonic acid was prepared by Brigl, Muhlschlegel and Schinle by benzoylation of the n-manno-n- oZa-heptononitrile the hexabenzoyl derivative was obtained. A series of benzoylated nitriles has recently been prepared by Restelli de Labriola and Deulofeu by treatment of the oximes of L-rhamnose, D-glucose, D-galactose and D-mannose with benzoyl chloride and pyridine. They were the sole products and were obtained in high yields. 

D-Galactose. Wohl and List prepared pentaacetyl-n-galactononitrile from the oxime in 40% yield. Degradation with ammonia-silver oxide gave 40% of n-lyxose diacetamide. Hydrolysis of the diacetamide with... 

This compound is easily available by the pyrolysis of D-galactose [25] or, on the small scale, by Angyal and Beveridge s method [26]. Regioselective catalytic oxidation led to the corresponding 5-ulose which, via the oxime and subsequent reduction, could be converted into inhibitor (5) in approximately 6% overall... 

D-Galactose, A108 Galactose oxime, AI19 Galactose semicarbazone, AL3 ... 

Hydrogenation of aldose oximes (aldoses D-arabinose, D-mannose and D-galactose) at 50 °C over 5 % Pt/C catalyst, under 100 bar hydrogen, resulted in quantitative conversion of the oximes to a mixture of mono- and dialditylamines from which the latter were isolated in fairly good yield (26-80%) [44]. 

The similar polarographic behavior of semicarbazones, hydrazones, phenylhydrazones, and oximes of D-glucose, D-galactose, and n-mannose was described in another paper. For the aldoses studied, the equilibrium and rate constants for the formation of their oximes, semicarbazones, and hydrazones were determined at several different pH values, and it was found that their reactivity increases in the order D-glucose < D-galactose < D-mannose < D-xylose < n-arabinose < D-ribose < D-lyxose. ... 

The monosaccharide composition of peat hydrolysates was successfully determined by g.l.c. of the trimethylsilylated oxime derivatives. Amongst the sugars recognized were o-xylose, L-arabinose, D-ribose, L-rhamnose, d-galactose, and D-glucose. 

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