Sulfuric Sugars and Their Derivatives. 12. Xanthogenic Glucose and its Cleavage into Glucothiose (1-Thio-Glucose)

Abstract : Since aceto-bromoglucose can be transformed smoothly to aceto-xanthogenic glucose with potassium-ethyl xanthogenate, a compound which apparently yields glucothiose upon saponification, it was felt that ethyl- xanthogenic glucose (hereafter called xanthogenic glucose) was indeed a favorable starting material for the convenient production of 1-thioglucose on one hand, and suited for the collection of experience in preliminary work aimed at the synthesis of mustard oil glycosides, on the other. The compound was obtained in two different dimorphous modifications, of which the one with the higher melting point was found to be stable at room temperature. Upon saponification with alkaline agents, especially with methyl alcoholic ammonia, free xanthogenic glucose in fact cannot be isolated, but glucothiose is obtained directly instead.