Triethylamine → Oleyl Glucose Acrylate

Participants

Reaction Steps

To glucose (10 g) in anhydrous DMF (100 ml) containing excess triethlamine was added freshly distilled oleyl chloride (1 mol. equiv.), followed by acryloyl chloride after one hour reaction. The mixture was stirred overnight and the solvent removed in vacuo. The product was purified by hexane filtration followed by chromatography on silica (1.5% methanol in methylene chloride). We have applied the same transformation technology to a pentahydroxylated sugar, glucose, as depicted in FIG. 37 to yield the glucose-based compound 31, which is a mixture of regio and stereo isomers. This material has three free hydroxyls (on average) per molecule, and has a more hydrophilic character.

Provenance & Evidence