Improved Synthesis of Glycosylamines and a Straightforward Preparation of N-acylglycosylamines As Carbohydrate-based Detergents

D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantitatively the corresponding glycosylamine when treated at 42 degrees C for 36 h with a commercial aqueous solution of ammonia in the presence of one equivalent of ammonium hydrogen carbonate. After lyophilisation, the residue (i.e., the pure glucosylamine) was dissolved in a mixture of ethanol and water, and treated with acyl chlorides to afford in a few minutes N-acylglucosylamines. Micellar properties of these amphiphilic derivatives were determined.