A. Lubineau et al., IMPROVED SYNTHESIS OF GLYCOSYLAMINES AND A STRAIGHTFORWARD PREPARATION OF N-ACYLGLYCOSYLAMINES AS CARBOHYDRATE-BASED DETERGENTS, Carbohydrate research, 266(2), 1995, pp. 211-219
D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantit
atively the corresponding glycosylamine when treated at 42 degrees C f
or 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 mixtur
e of ethanol and water, and treated with acyl chlorides to afford in a
few minutes N-acylglucosylamines. Micellar properties of these amphip
hilic derivatives were determined.