Sodium Bicarbonate → HCID 57867354, compound

Participants

Reaction Steps

To a solution of (2R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-3,4-dimethyl-tetrahydrofuran-3-ol (about 6.3 g, 14.5 mmol) in tetrahydrafuran (about 100 ml) at about 0° C. was added 1N tetra butyl ammonium fluoride solution (about 14.5 ml, 14.5 mmol) drop wise for about 10 minutes and stirred at room temperature for about 1.5 hours. Completion of the reaction monitored by thin-layer chromatography and neutralized with saturated sodium bicarbonate. Aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with water, brine and dried over sodium sulphate and concentrated under reduced pressure, purified by silica gel column chromatography using 50% ethyl acetate: hexane as eluent furnished the title compound (2.8 g) as a colorless liquid. Yield: 99%; 1H NMR (300 MHz, CDCl3): δ 4.84 (d, 1H, J=11.1 Hz), 4.11 (m, 1H), 3.88-3.87 (m, 2H), 3.46 (s, 3H), 3.35 (s, 1H), 2.05 (m, 1H), 1.40 (d, 3H, J=23.4 Hz), 1.27 (d, 3H, J=2.1 Hz); Mass: [M+Na]+: 217 (100%).

Provenance & Evidence