Abstract
THE usual reaction product of the treatment of the acylated nitriles of aldonic acids with ammonia are the aldose diacetamides1. A variation of this reaction was found when Hockett and Chandler2, by treating hexa-acetyl-D-α-glucoheptonic acid nitrile with ammonia, obtained N-acetyl-D-glucofuranosylamine. The same product resulted from the action of ammonia on penta-acetyl-aldehydo-D-glucose. Later, Niemann and Hays3 prepared N-acetyl-D-glucofuranosylamine by the action of methanolic ammonia on penta-acetyl-D-β-glucose, a reaction that produced the transformation of the original pyranose ring of the acetylated glucose into a furanose structure.
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References
Full bibliography in Deulofeu, “Advances in Carbohydrate Chemistry”, 4, 119 (New York Academic Press, 1949).
Hockett and Chandler, J. Amer. Chem. Soc., 66, 957 (1944).
Niemann and Hays, J. Amer. Chem. Soc., 67, 1302 (1945).
Brigl, Mühlschlegel and Schinle, Ber., 64, 2921 (1931).
Isbell and Frush, J. Amer. Chem. Soc., 71, 1579 (1949).
Hockett, Deulofeu and Deferrari, J. Amer. Chem. Soc., 72, 1840 (1950).
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DEULOFEU, V., DEFERRARI, J. Preparation of D-Glucose Dibenzamide from Pentabenzoyl-D-α-Glucose. Nature 167, 42 (1951). https://doi.org/10.1038/167042a0
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DOI: https://doi.org/10.1038/167042a0
