Reaktion #569854

Reaktionsgleichung

toluene isopropanol

octadecanoyl chloride

N-octadecyl-N-3,6-dioxodecanoyl-β-D-glucopyranosylamine

triethylamine

→

N-Octadecyl-N-3,6-dioxodecoyl-(6-stearyl-β-D-glucopyranosyl)-amine

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe solid is filtered off with suction
2. 2
   Sonstigethe solvent is removed in a water-pump vacuum
3. 3
   SonstigeThe residue is chromatographed on a column
4. 4
   workup.ADDITIONcontaining 250 g of silica gel
5. 5
   Sonstigeare obtained

Vorschrift

1.2 g (0.004 mol) of octadecanoyl chloride and 2.0 g (0.0034 mol) of N-octadecyl-N-3,6-dioxodecanoyl-β-D-glucopyranosylamine in 50 ml of tetrahydrofuran are initially taken, and 0.4 g of triethylamine (0.004 mol) is added at 0° C. The mixture is stirred for 1 day at 20° C., the solid is filtered off with suction and the solvent is removed in a water-pump vacuum. The residue is chromatographed on a column containing 250 g of silica gel, using as mobile phase 10:1 toluene/isopropanol, and 1.9 g (65% of theory) of N-octadecyl-N-3,6-dioxodecoyl-(6-stearyl-β-D-glucopyranosyl)-amine are obtained, having an Rf value of 0.296 (6:1 toluene/isopropanol).

Quelle