Triphenylphosphine → HCID 15108965, compound

Participants

Reaction Steps

1.28 g (10.0 mmol) of 1,6-anhydro-β-D-threo-hex-3-enopyranose, 5.25 g (20.0 mmol) of triphenyl phosphine, and 3.64 g (20.0 mmol) of 3,5-dimethoxybenzoic acid were added to 16 ml of dry THF, and a solution obtained by dissolving 3.48 g (20.0 mmol) of diethylazodicarboxylate in 16 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 45 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 obtain 2.45 g (yield: 83.7%) of 1,6-anhydro-3,4-dideoxy-2-O-(3,5-dimethoxybenzoyl)-β-D-erythro-hex-3-enopyranose. This product was recrystallized from a solvent mixture of hexane and diethyl ether.

Provenance & Evidence