反应详情

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-methoxybenzyl acetate (7) (333 mg, 0.632 mmol) was suspended in methanol (2 ml), and sodium methoxide 5 M methanol solution (20 μl, 0.10 mmol) was added while cooling in an ice bath. The ice bath was removed and the mixture was warmed to room temperature and stirred for 2 hours. Sodium methoxide 0.5 M methanol solution (0.12 ml, 0.06 mmol) was further added and the mixture was stirred for 1 hour. The reaction solution was neutralized with a strong acidic cation exchange resin (Amberlite IR120B H AG). The resin was filtered off, and the filtrate was concentrated under reduced pressure to give 4-(β-D-glucopyranosyloxy)-3-methoxybenzyl alcohol (8) (147 mg, 0.465 mmol, yield 74%) as a colorless solid.

1. temperaturewhile cooling in an ice bath
2. customThe ice bath was removed
3. stirringthe mixture was stirred for 1 hour
4. filtrationThe resin was filtered off
5. concentrationthe filtrate was concentrated under reduced pressure