Methanol → HCID 7784447, compound

Participants

Reaction Steps

To a stirred solution of the allose diacetonide (19.6 g, ca. 75 mmol) in THF-DMF (500 mL, 4:1 v/v) at and under argon was added a 60% sodium hydride dispersion in mineral oil (6.0 g, 150 mmol) portionwise over 30 min. The resulting mixture was allowed to warm to room temperature over 1h, then it was recooled to 0° C. before benzyl bromide (25.7 g, 17.9 mL, 150 mmol) and t-n-butylammonium iodide (1.0 g) were added. The resulting mixture was allowed to warm to room temperature and stir for 16 h. The reaction mixture was cooled to 0° C. and anhydrous methanol (20 mL) was cautiously added over 30 min. The resulting mixture was allowed to warm to room temperature and stir for 1 h before the THF was removed by rotary evaporation. The residue was suspended in H2O (250 mL) and extracted with ethyl acetate (4×200 mL). The combined organic fractions were washed with H2O (500 mL) and brine (200 mL), dried over Na2SO4, filtered, and concentrated to give the crude 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose as a clear, yellow oil (46.8 g). This material was used without further purification. ##STR64##

Provenance & Evidence