Tetrabutylammonium Fluoride → methyl 2,3,4-tri-O-benzyl-beta-D-glucopyranoside

Participants

Reaction Steps

To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (2.81 g, 3.98 mmol) in dry THF (40 ml, 0.1 M) at room temperature was added tetrabutyl ammonium fluoride (4.37 ml, 4.37 mmol, 1 M solution in THF). After stirring for 3 hours, the reaction solution was diluted with ethyl acetate (300 ml) and washed with water (1×100 ml) and saturated aqueous NaCl (1×100 ml), and dried with magnesium sulfate. Concentration and flash chromatography (silica, 50% ether in petroleum ether) provided pure target compound (1.62 g, 88%) as a white solid.

Provenance & Evidence