Abstract
Amphiphilic N-acyl- D-glucosamines 1 were prepared by acylation of 2-amino- 2-deoxy-D-glucosamine with the anhydrides of the homologous long chain C 8-C 16-carboxylic acids. These compounds react in anhydrous hydrogen fluoride very slowly with formation of 3,6-anhydro-D-glucofuranosyl derivatives 2. This ring contraction takes place very rapidly in the presence of 1 molar equivalent of formic acid, according to [J. Defaye, A. Gadelle and C. Pedersen, Carbohydr. Res., 205 (1990) 191]. The corresponding oxazoline derivatives 3 can be isolated from the HF-phase. ▪ The amphiphilic derivatives 3 were used to determine their c.m.c. data in anhydrous HF with the help of the solubilisation method [see also D. Peters, J. Holz and R. Miethchen, J. Fluorine Chem., 50 (1990) 117].
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