Methanol → methyl L-xylofuranoside

Participants

Reaction Steps

L-Xylose (1, 25 g, 167 mmol) was stirred for 5 hours in 0.5% hydrogen chloride in methanol (675 mL) at room temperature and then neutralized with Amberlite IRA-400 OH anion exchange resin. The filtrate and washings were combined and evaporated to dryness and the crude product was purified by silica gel chromatography (CHCl3/MeOH, 92:8) to afford 26.2 g of methyl L-xylofuranoside (2, 95% yield) as an α and β (1:1) mixture. MS 164 (M)+, 165 (M+H)+, 133 (M-OCH3)+.

Provenance & Evidence