Potassium Carbonate → 2-o-beta-d-Glucopyranosyl-l-ascorbic acid

Participants

Reaction Steps

After dissolving 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)ascorbic acid (300 mg, 0.6 mmol) in methanol (10 ml), a solution of potassium carbonate (600 mg) in water (9 ml) was added and the mixture was stirred for 30 minutes. The reaction solution was neutralized with IR-120(H+), the resin was filtered off, and washing was performed with methanol and a 50% methanol aqueous solution. The filtrate and washing solution were combined and concentrated, and then water was added and the mixture was lyophilized to obtain 2-O-(β-D-glucopyranosyl)ascorbic acid as amorphous crystals (190 mg, 100% yield). 1H-NMR (δppm, D2O); 3.1-3.3 (4H, m), 3.4-3.5 (3H, m), 3.58 (1H, d), 3.80 (1H, t), 4.61 (1H, d), 4.66 (1H, d). FABMS (−) m/z: 337.

Provenance & Evidence