The crystalline glucose-aniline bisulphite
addition compound, D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl
anilinium sulphonate, was prepared from the reaction of D-glucose with aniline
bisulphite in water and in methanol. The D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl
piperidinium sulphonate was prepared by adding piperidine bisulphite to
preformed N-phenyl-D-glucosylamine. Other new compounds of similar structure
were prepared from the reaction of aniline bisulphite with D -galactose and
D-mannose.
cycloHexylamine bisulphite reacted with
D-glucose to form crystalline D-glycero-D-ido-1,2,3,4,5,6-hexahydroxyhexyl
cyclohexylammonium sulphonate. When treated with aniline this compound formed D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl
cyclohexylammonium sulphonate.
The D-glycero-D-ido-1-anilino-2,3,4,5,6-pentahydroxyhexyl
potassium and anilinium sulphonates were interconverted by use of a
cation-exchange resin. Acetylation of the anilinium sulphonate in pyridine gave
the tetra-acetate of N-phenyl-D-glucosylamine.