The conversion of D-Glucono-1,5-lactone (cas 1335-57-5) into an α-pyrone derivative

Add time:09/05/2019    Source:sciencedirect.com

Treatment of D-Glucono-1,5-lactone (cas 1335-57-5) (3) with excess of acetic anhydride in anhydrous pyridine at room temperature afforded the tetra-acetate and 2,4,6-tri-O-acetyl-3-deoxy-d-erythro-hex-2-enono-1,5-lactone (1). On prolonged reaction or at 80°, 3-acetoxy-6-acetoxymethylpyran-2-one (5) was the unexpected main product. The mechanistic implications of the conversion of 1 → 5 are discussed.

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