Sodium hydride → methyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-D-glucopyranoside

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Reaction Steps

Methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (1.16 g, 2.5 mmol) was dissolved in DMF (10 ml) and thereto was added sodium hydride (60% in oil, 120 mg, 3.00 mmol) at 0° C., followed by stirring for 15 min. Then 4-azido-3-chlorobenzyl bromide (740 mg, 3.00 mmol) was added portionwise. The resulting mixture was stirred at 0° C. for 30 min and at room temperature for 3 hr. Ice-water was added and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to give the title compound as a yellow oil (1.48 g, yield 94%).

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