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

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Abstract

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).

Abstract

Several 6-amido-6-deoxy derivatives of methyl α-d-glucopyranoside and d-glucopyranose were prepared from 6-azido-6-deoxy intermediates. The Staudinger reaction (PPh3, carboxylic acid or acid chloride) or the addition of n-heptanol on the 6-deoxy-6-isocyano derivatives, obtained from the 6-azido analogues, completed the synthesis. The Krafft temperatures and surfactant properties of these compounds are reported.

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