Synthesis and surface-active properties of amphiphilic 6-aminocarbonyl derivatives of d-glucose

Several 6-amido-6-deoxy derivatives of methyl α-d-glucopyranoside and d-glucopyranose were prepared via peracetylated 6-azido-6-deoxy or 6-deoxy-6-isocyanato intermediates. These compounds displayed high Krafft temperatures which could result from hydrogen bonding between NH and O-5. Their tensio-active properties above the Krafft temperature were compared with Hecameg (methyl 6-O-(N-heptylcarbamoyl)-α-d-glucopyranoside).