Formic Acid → Phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranoside

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Reaction Steps

To a solution of phenyl 2,3,4-tri-O-(4-methoxybenzyl)-6-O-triphenylmethyl-1-thio-β-D-glucopyranoside (7) (3.44 g, 3.93 mmol) in ether (8 ml) was added formic acid (8 ml), and the resulting mixture was stirred at room temperature for 5 hr. The reaction mixture was washed successively with water, saturated aqueous sodium hydrogen-carbonate solution and saturated brine, and the solvent was evaporated under reduced pressure. The residue was suspended in a mixture of ethanol (5 ml) and 1N aqueous sodium hydroxide solution (5 ml), and the suspension was stirred overnight at room temperature. Ethanol was evaporated under reduced pressure and the resulting suspension was extracted twice with ether. The combined ether layers were washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1) to give phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (8) (1.28 g, yield 51%) as white crystals.

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