Triphenylphosphine → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-methoxybenzyl acetate

Participants

Reaction Steps

Under an argon atmosphere, 2,3,4,6-tetra-O-acetyl-D-glucopyranose (2) (576 mg, 1.65 mmol) was dissolved in toluene (5 ml) at room temperature, and triphenylphosphine (423 mg, 1.61 mmol) and 4-acetoxymethyl-2-methoxyphenol (6) (204 mg, 1.04 mmol) were added. Then, the reaction mixture was cooled in an ice bath, diethyl azodicarboxylate 2.2 M toluene solution (0.75 ml, 1.65 mmol) was added dropwise, the ice bath was removed and the mixture was warmed to room temperature and stirred for 3 hours. The reaction solution was concentrated under reduced pressure, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (gradient; ethyl acetate:n-hexane=20:80→61:39) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-methoxybenzyl acetate (7) (335 mg, 0.637 mmol, yield 61%) as a colorless oil.

Provenance & Evidence