Sodium Hydroxide → HCID 69820884, compound

Participants

Reaction Conditions

Reaction Steps

A mixture that consists of 54.1 g (100 mmol) of 2,3,4,6-tetra-O-benzylglucopyranose, 1.39 g (5 mmol) of tetrabutylammonium chloride and 24 g (600 mmol) of fine-powder sodium hydroxide in 350 ml of dichloromethane is cooled to 10° C. At 10° C., 41.3 g (140 mmol) of 1-(dimethyl-tert-butylsilyloxy)-6-bromohexane, dissolved in 100 ml of dichloromethane, is added in drops over 50 minutes while being stirred vigorously. It is stirred for three hours at 10° C. 350 ml of dichloromethane is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is taken up in 350 ml of acetonitrile, and 52.3 g (200 ml) of tetrabutylammonium fluoride is added (as a monohydrate). It is stirred for three hours at 50° C. The solution is evaporated to the dry state, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/ethanol=20:1).

Provenance & Evidence