Glucose anilide

In certain of their reactions, the substances behave as Schiff bases. However, since methylation by the use of methyl iodide and silver oxide and subsequent hydrolysis of the glucosylaniline (glucose anilide) (I) lead to tetra-O-methylglucopyranose (III) 16) the compound probably has a pyranose ring 16). The identical tetra-O-methyl pyranose ether (II) was obtained by methylation of Ar-phenyl-D-glucosylamine (I) by the use of dimethyl sulfate and sodium hydroxide, though only in 25% yield 17a, b). 

Simple Aromatic Amines.—Crystalline anilides of 2-desoxy-D-galac-tose,223 2-desoxy-D-glucose,120 223 2-desoxy-D-xylose,60 and 2-desoxy-D-158 and -L-ribose112 have been obtained by the usual method of synthesis of... 

All these substances reduce hot Fehling solution, though the anilide LXXIX required heating at 95° for two minutes. Treatment with 0.003 M barium methoxide in dry methanol at room temperature decomposed 3-keto-n-butyl 0-D-glucopyranoside tetraacetate (X), to yield D-glucose and methyl vinyl ketone (LXXX). 

Methylation of stachyose and subsequent hydrolysis, by Onuki,20 gave 2,3,4,6-tetra-O-methyl-D-galactose (identified as the crystalline anilide), a tri-O-methyl-D-galactose and a tri-O-methyl-D-glucose (which were converted into the 2,3,4,6-tetra-O-methyl derivatives, and characterized as the crystalline anilides), and 1,3,4,6-tetra-O-methyl-D-fructose, a sirup which agreed in properties with the authentic material. 

A large number of organic compounds, including aldehydes, ketones, lactones, carboxylic acids, chlorides and anhydrides, esters, amides, anilides and alcohols, ketals, epoxides, nitro compounds, glucose, ascorbic acid, and some ethers, have been analyzed by Dahn et al. (1959)... 

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