Tetrabutylammonium Fluoride → (1S,3R,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-one

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Reaction Steps

To a solution of (1R,3R,4R,5S)-3,4-dibenzyloxy-1-[(tert-butyl(dimethyl)silyl)oxymethyl]-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-2-one 28f (15.9 g, 21.8 mmol) in tetrahydrofuran (40 mL) was added tetrabutylammonium fluoride (48 mL, 43.6 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at room temperature for 2 hours and extracted with ethyl acetate (100 mL×2). The combined organic phases were washed with water (100 mL×3) and then saturated aqueous sodium chloride (100 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 28g as colorless oil (13.4 g, 100%). The crude product was used for next step without further purification. The compound was characterized by the following spectroscopic data: 1H NMR (600 MHz, CDCl3) δ (ppm): 7.31 (d, 2H), 7.29-7.22 (m, 6H), 7.13 (m, 1H), 7.07 (m, 2H), 6.98 (d, 2H), 6.75 (d, 2H), 6.68 (d, 2H), 5.28 (s, 1H), 4.93 (d, 1H), 4.59 (d, 1H), 4.31 (m, 2H), 4.10 (d, 1H), 3.99 (m, 2H), 3.96-3.92 (m, 3H), 3.88 (m, 3H), 1.31 (t, 3H).

Provenance & Evidence