(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane

100-39-0

117641-39-1

110567-22-1

General procedure: sodium hydride (55-65%, 0.93 kg, 21.3-25.2 mol) was suspended in anhydrous tetrahydrofuran (25 kg) and stirred for 10 min at room temperature. A solution of (1S,2R,3S,5R)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexan-3-ol (2.99 kg, 12.3 mol) in tetrahydrofuran was added slowly and dropwise at 20-30 °C. Subsequently, benzyl bromide (3.14 kg, 18.3 mol) was added dropwise over 2-3 hours at room temperature. After completion of the reaction, the reaction was quenched by the addition of anhydrous ethanol (1.5 kg) and stirred at 10 °C. The solvent was removed by distillation under reduced pressure and the residue was dissolved in ethyl acetate. The resulting solution was washed with saturated saline (10 kg, 3 times) and the organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give (1S,2R,3S,5R)-3-(phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane (4.4 kg) as a reddish brown oil.1H NMR (400 MHz, DMSO-d6). δ 1.923-1.960 (1H, m), 2.026-2.087 (1H, m), 2.448-2.436 (1H, m), 3.324-3.520 (3H, m), 3.520 (1H, s), 3.865-3.884 (1H, m), 4.322-4.391 (2H, m), 4.480 (2H, s), 7.251-7.373 (10H, m). HRMS (ESI): m/z calcd for C20H22O3Na [M+Na]+ 333.1467, found 333.1463.