Benzoic Acid → 1,6-anhydro-3,4-dideoxy-2-O-(benzoyl)-beta-D-erythro-hex-3-enopyranose

Participants

Reaction Steps

2.56 g (20.0 mmol) of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose, 10.49 g (40.0 mmol) of triphenyl phosphine, and 4.88 g (40 mmol) of benzoic acid were added to 32 ml of dry THF, and a solution obtained by dissolving 6.97 g (40.0 mmol) of diethylazodicarboxylate in 32 ml of dry THF was gradually dropped in the above mixture in a nitrogen-sealed ice-water bath. The resultant solution was stirred at room temperature for 23 hours. The solvent was distilled from the reaction solution at a reduced pressure. Triphenyl phosphine oxide as a byproduct was eliminated from the residue using a silica gel column (eluent: chloroform). The solvent was distilled from the resultant eluate at a reduced pressure, and the residue was purified using a silica gel column (hexane:ethyl acetate=5:1 to 4:1). The purified residue was recrystallized from a solvent mixture of hexane and diethyl ether (a mixing ratio of 1:1) to obtain 3.48 g (yield: 74.9%) of 1,6-anhydro-3,4-dideoxy-2-O-(benzoyl)-β-D-erythro-hex-3-enopyranose.

Provenance & Evidence