反应详情

20 grams of 1-eicosanyl-sn-glycerol and 18 grams of triphenylchloromethane were added to a mixture of 400 ml dry tetrahydrofuran (THF) and 100 ml dry acetonitrile. 15 ml of dry triethylamine was added, and the reaction mixture was refluxed for 17 hours. The reaction mixture was then cooled to room temperature, poured on ice (500 grams), transferred to a separatory funnel, and extracted thrice with 200 ml diethyl ether. The organic phase was washed consecutively with 150 ml water, twice with 150 ml dilute (1.5%) H2SO4, 150 ml water, 150 ml concentrated aqueous sodium bicarbonate, and again with 150 ml water. The solution was then dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained residue, a brown oil, was dissolved in 300 ml ethyl acetate, and cooled at −20° C. overnight. The mixture was centrifuged (3,500 rotations per minute) at −10° C., and the mother liquid was poured of. The obtained solid was dissolved in hexane and refrigerated (5±3° C.) overnight. Filtration of the precipitate yielded 26.0 grams of pure (R)-1-eicosanyl-3-trityl-sn-glycerol as an off-white solid. The yield was 79%.

1. temperaturethe reaction mixture was refluxed for 17 hours
2. additionpoured on ice (500 grams)
3. customtransferred to a separatory funnel
4. extractionextracted thrice with 200 ml diethyl ether
5. washThe organic phase was washed consecutively with 150 ml water, twice with 150 ml
6. additiondilute (1.5%) H2SO4, 150 ml water, 150 ml concentrated aqueous sodium bicarbonate
7. dry with materialThe solution was then dried over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure
9. dissolutionThe obtained residue, a brown oil, was dissolved in 300 ml ethyl acetate
10. temperaturecooled at −20° C. overnight
11. customat −10° C.
12. additionthe mother liquid was poured of
13. dissolutionThe obtained solid was dissolved in hexane
14. customrefrigerated (5±3° C.) overnight
15. filtrationFiltration of the precipitate