Improved synthesis of glycosylamines and a straightforward preparation of N-acylglycosylamines as carbohydrate-based detergents

Article abstract of DOI:10.1016/0008-6215(94)00275-K

D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantitatively the corresponding glycosylamine when treated at 42 deg C for 36 h with a commercial aqueous aolution 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 proporties of these amophiphilic derivatives were determined.Keywords: Glycosylamines; N-Acylglycosylamines; Non-ionic detergents; Carbohydrate-based detergents; Surfactants