BYPRODUCTS IN THE PREPARATION OF PENTA-O-ACETYL-D-HEXONONITRILES FROM D-GALACTOSE AND D-GLUCOSE

Article abstract of DOI:10.1016/0008-6215(83)88240-8

The procedures commonly employed for preparing per-O-acetylated aldononitrile derivates of D-galactose and D-glucose for use in g.l.c. analysis involve oxime formation, and acetylation.They do not, however, give the nitriles as the sole products, as is generally assumed.Instead, N-hydroxy-D-glycosylamine hexaacetates are formed as byproducts, in part by a kinetically controlled ring-closure of the sugar oxime, concomitant with acetylation.From preparative isolation of the products, D-galactose gave the nitrile (67 percent) and the β-furanose (16 percent), α-furanose (1 percent), and β-pyranose (2 percent) isomers of the cyclic hexaacetate, whereas D-glucosegave the nitrile (63 percent), and the β-furanose (14 percent), and β-pyranose (8 percent) isomers.