反应详情

温度

0 °C

Under a nitrogen atmosphere, 80.0 g (0.251 mol) of β-xylose tetraacetate and 106 g (0.327 mol) of 5,9,13,17-tetramethyloctadec-4-en-1-ol was dissolved in dry acetonitrile (0.30 L), and stirred for 30 min. After the solution was cooled to 0° C., 38 mL (0.30 mol) of boron trifluoride diethyl etherate complex was added. The reaction mixture was allowed to warm up to room temperature while being stirred overnight before addition of 70 mL (0.50 mol) of triethylamine at 0° C. The resulting solution was diluted with ethyl acetate, and washed with water, 3M hydrochloric acid (twice), saturated sodium bicarbonate aqueous solution (twice), and saturated brine, successively, and dried over magnesium sulfate. After filtration, the filtrate was concentrated to obtain 161.95 g of the title compound as a crude product. A part of the crude product was purified by silica gel column chromatography (hexane/ethyl acetate 85:15). The results of NMR analysis of the resulting compound are as shown below.

1. addition38 mL (0.30 mol) of boron trifluoride diethyl etherate complex was added
2. temperatureto warm up to room temperature
3. washwashed with water, 3M hydrochloric acid (twice), saturated sodium bicarbonate aqueous solution (twice), and saturated brine
4. dry with materialsuccessively, and dried over magnesium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate was concentrated