Reaction Steps
To a stirred solution of the product from step A (1.3 g, 1.8 mmol) in tetrahydrofuran (16 mL) at 0° C. was added dropwise tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran; 2.2 mL, 2.2 mmol). The reaction mixture was warmed to room temperature and stirred for 4 h. Then it was concentrated and the crude material obtained was purified by flash column chromatography (eluent: hexanes/ethyl acetate 100:0 to 75:25) to give compound (2-chloro-5-((2S,3R,4S,5R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol (0.81 g, 94%) as a colorless syrup: 1H NMR (CDCl3, 500 MHz) δ 7.54 (br d, J=2.0 Hz, 1H), 7.33 (d, J=8.2 Hz, 1H), 7.28 (dd, J=8.2, 2.0 Hz, 1H), 4.91 (d, J=6.4 Hz, 1H), 4.89 (d, J=6.3 Hz, 1H), 4.87 (d, J=6.3 Hz, 1H), 4.78-4.76 (m, 3H), 4.65 (s, 2H), 4.47 (d, J=6.5 Hz, 1H), 4.19 (d, J=9.5 Hz, 1H), 4.14-4.10 (m, 2H), 3.92 (dd, J=11.3, 1.6 Hz, 1H), 3.76 (t, J=8.8 Hz, 1H), 3.71 (dd, J=11.2, 5.2 Hz, 1H), 3.63-3.58 (m, 2H), 3.53 (t, J=9.4 Hz, 1H), 3.452 (s, 3H), 3.448 (s, 3H), 3.34 (s, 3H), 2.82 (s, 3H); ESI MS m/z 481 [M+H]+.
