Acetic Anhydride → (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one

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Reaction Steps

Acetic anhydride (7.40 mL, 78 mmol, commercially available from Sigma Aldrich) was added to a solution of (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (1.70 g, 3.91 mmol) in DMSO (12 mL), and the resulting mixture was stirred for 24 h at P. EtOAc was added, and the mixture was washed with water (3×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography (0 to 40% EtOAc/hexanes gradient) to give (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one as a colorless oil (1.06 g, 62.6% yield). ESI (M+H) 433.1; calc for C27H28O5 432.2.

Provenance & Evidence