Benzyl Bromide → (2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate

Beteiligte Stoffe

Reaktionsschritte

To a solution of (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylic acid (1 g, 5.15 mmol) and TBAF in THF (6.18 mL, 6.18 mmol) in DMF (7 mL) was slowly added (bromomethyl)benzene (0.925 g, 5.41 mmol) at 0° C. The clear solution was warmed up to room temperature slowly and let it stir for 17 hours. TLC indicated the reaction was completed (20% iPrOH/CH2Cl2). The solvent was removed and the reaction residue was purified by silica gel chromatography with 10-20% iPrOH/CH2Cl2 to provide the desired product as a colorless oil (950 mg, 65%). LCMS: m/e 283.31 (M−H)−, 2.55 min (method 10).

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