Allyl Alcohol → HCID 67157178, compound

α-D-cellobiose octacetate (48.59 g, 71.6 mmol) was dissolved in methylene chloride (600 mL), and allyl alcohol (29 mL, 0.43 mol) and trimethylsilyl trifluoromethanesulfonate (16 mL, 86.0 mmol) were added thereto under ice-cooling, followed by stirring of the mixture at room temperature for 1.5 hours. Water (200 mL) was added to the reaction mixture and the mixture was extracted with methylene chloride (200 mL). After the extract was washed with saturated brine (100 mL) and dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was dissolved in methanol (300 mL) and sodium methoxide (28 mL, 0.14 mol) was added thereto under ice-cooling, followed by stirring of the mixture at room temperature for 2 hours. After Dowex 50w×8 was added thereto until the reaction mixture became neutral and it was filtered, the solvent was distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (ethyl acetate:methanol:water, 8:2:1, V/V) to obtain the desired title compound (24.8 g, yield 91%) as pale yellow amorphous matter.

1. temperatureunder ice-cooling
2. extractionthe mixture was extracted with methylene chloride (200 mL)
3. washAfter the extract was washed with saturated brine (100 mL)
4. dry with materialdried with anhydrous sodium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. dissolutionThe residue was dissolved in methanol (300 mL)
7. temperatureunder ice-cooling
8. stirringby stirring of the mixture at room temperature for 2 hours
9. filtrationit was filtered
10. distillationthe solvent was distilled off under reduced pressure
11. customThe residue was purified

ORD record

ord-4724b5e896d24eafb8d7b4140e03b0b2

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632930B2