3,4-dihydro-2H-pyran → 6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

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Reaction Steps

To a solution of hexahydrofuro[3,2-b]furan-3,6-diol (10.0 g, 68.50 mmol) in DCM (150 mL) was added PPTs (1.7 g, 6.85 mmol) at rt followed by DHP (6.0 g, 71.90 mmol) slowly in 2 h, and then the mixture was stirred at rt overnight and concentrated in vacuo. The residue was dissolved in water (150 mL), and extracted with EtOAc (150 mL×3). The combined organic phases were washed with brine (300 mL), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=1/1) to give the title compound as a white solid (7.1 g, 45%).

Provenance & Evidence