Nitriles of aldonic acids

Deulofeu, Venancio, The Acylated Nitriles of Aldonic Acids and Their Degradation, IV, 119-151... 

Afterward, Behrend found that the nitrile is also produced when o-glucose oxime is treated with pyridine and acetic anhydride, and this method has been extended to the preparation of other nitriles of aldonic acids. ... 

Apart from the general procedures that have been described, nitriles of aldonic acids are capable of other reactions that also lead to degradations. 

For a long time, this reaction was conducted exclusively with acety-lated nitriles of aldonic acids, and the products obtained were known in general as "aldose-amides. Fischer2 used this reaction to transform tetra-O-acetyl-L-rhamnononitrile into l,l-bis(acetamido)-l,5-dideoxy-L-arabinitol, whose subsequent hydrolysis and oxidation allowed him to determine the configuration of dextro-tartaric acid (L-threaric acid). 

Brigl and coworkers9 discovered the first example showing that the formation of aldose amides is not restricted to the degradation of acylated nitriles of aldonic acids. By ammonolysis of 2,3,4,5,6-penta-O-benzoyl-aldehydo-n-glucose (16), they obtained l,l-bis(benz-amido)-l-deoxy-D-glucitol (17). 

Deulofeu, Venancio, The Acylated Nitriles of Aldonic Acids and Their Degradation, 4, 119-151 Dimler, R. J., 1,6-Anhydrohexofuranoses, A New Class of Hexosans, 7, 37-52 Doudoroff, M. See Hassid, W. Z. Dubach, P. See Mehta, N. C. 

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