2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → 1,3,4,5-Tetra-O-benzyl-D-glucitol

Participants

Reaction Steps

To a stirred solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol 1 (25 g, 46.24 mmol) in THF (310 mL) was added solid LiAlH4 (6.14 g, 161.84 mmol) portion-wise at 0° C. and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was cooled to 0° C. and carefully quenched with with saturated Na2SO4 solution (35 mL) and the reaction mixture was stirred at room temperature for 30 min. Solid was filtered through a celite pad and the filtrate was diluted with ethyl acetate (250 mL). Organic part was separated and washed with saturated aqueous solution of NH4Cl (3×100 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure to get crude was purified by column chromatography using 100-200 mesh silica gel and eluting with 12% EtOAc/hexane to get (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol 2 (24 g, 95%) as sticky oil.

Provenance & Evidence