D-Glucose dibenzamide

In the case of the above mentioned benzoyl-D-glucose derivatives a correlation was found between the formation of D-glucose dibenzamide and the permanent or transitory existence of a free aldehyde group. The same behavior was noted for triacetyl-oZdehydc-L-erythrose (XLI), which by the action of ammonia produces L-erjrthrose diacetamide (XLII). Isbell and Frush have obtained a similar result in the case of tetraacetyl-oWe/it/do-L-arabinose which, when treated with methanolic ammonia, gave L-arabinose diacetamide in 53 % yield. 

Later work by Deulofeu and Deferrari further supports this mechanism they showed that D-glucose dibenzamide results from the respective action of ammonia on the pentabenzoates of a-n-glucopyranose, 8-D-gluco-... 

Evidence that the aldose diacetamides are derived from the union of preformed amides with the aldehydo form of the aldose was obtained many years later. Brigl, Miihlschlegel and Schinle, obtained n-glucose dibenzamide (XXXVIII) by the action of methanolic ammonia on penta-benzoyl-oWe%do-D-glucose (XXXVII). They studied the same reaction... 

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