CHEMISTRY OF 1,1-BIS(ACYLAMIDO)-1-DEOXY-ALDITOLS - BASE-CATALYZED TRANSFORMATIONS IN PROTIC SOLVENTS

The posibility of nucleophilic displacements of C-1-acylamido groups i n 1,1-bis(acylamido)-alditols was investigated in protic solvents. The reactions of 1,1-bis(benzamido)-1-deoxy-D-glucitol with basic reagent s such as methoxy de or cyanide ions and with triethylamine showed com plex patterns of: a) nitrogenated monosaccharides such as alpha-D-gluc opyrano)-2-phenyl-[1,2-d]-oxazolidine, -beta-D-glucofurano)-2-phenyl-[ 1,2-d]-oxazolidine, and N-benzoyl-beta-D-glucopyranosylamine; b) reduc ing sugars (glucose, mannose and fructose); c) nitrogenated melanoidin s. The routes leading to (b) and (c) predominate in the higher polar m edia, and are known reactions of sugars in alkaline solution. The rear rangements leading to nitrogenated sugars evidenced a particular behav ior of bis-acylamido alditols and are significant in the less-polar so lvents or by reaction with weak nucleophiles.