Saccharin Glucosides

Saccharin Glucosides.—3-Chloro-l,2-benzisothiazole 1,1-dioxide (64) reacts with nucleophiles (ROH, RSH, or RNHg) to yield products derived from the imide form of saccharin (63). Its reaction in pyridine with 2,3,4,6-tetra-O-methyl(or -acetyl)-ajS-D-glucopyranose similarly gives the readily crystallizable 3-(a-D-glucosyl)-l,2-benzisothiazole 1,1-dioxides (67), irrespective of the configuration of the monosaccharide used. In the absence of base, the reaction 

The reaction can be applied to other carbohydrates and two or three saccharin-residues may be introduced. It is useful for characterizing monosaccharides which may be recovered by acid hydrolysis.  

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In a later investigation comparing the influence of different alkaline media, it was found that the methyl 3-keto-/3-n-glucoside (91 A) is degraded somewhat more slowly in sodium hydroxide (0.018 N, at 23°) than in lime-water of the same concentration. Further reaction of the dicarbonyl intermediate (112 B), to give acids, was much faster with lime-water, in accordance with the established catalyzing effect of calcium on saccharinic acid formation." ... 

Heat treatment of alkaline solutions (pH >12) at >110 °C causes splitting of the glucosidic linkage, isomerization, enolization and destruction to C3-and C2-compounds D,L- lactic acid, acetic acid, saccharinic acids or the corresponding aldehydes. Further aldolic condensation leads to - caramel color. 

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