(2S)-3-octadecoxypropane-1,2-diol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the procedure of the reference [FEBS Letters, Vol. 116, 161 (1980)], D-mannitol was used as a starting material to give 25 g of the desired compound (needles) through 1,2-isopropylidene-sn-glycerol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the procedure of the reference [FEBS Letters, Vol. 116, 161 (1980)], D-mannitol was used as a starting material to give 25 g of the desired compound (needles) through 1,2-isopropylidene-sn-glycerol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39 grams (113 mmol) of (S)-1-octadecyl-glycerol and 40 grams (137 mmol) of triphenylchloromethane were added to a mixture of 500 ml of dry THF and 130 ml of dry acetonitrile. 32 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 (1 kilogram), transferred to a separatory funnel and extracted twice with 200 ml diethyl ether. The organic phase was washed consecutively with 200 ml water, twice with 100 ml dilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate, and again with 200 ml water. The solution was then dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue, a brown oil, was dissolved in 250 ml ethyl acetate and cooled to −20° C. overnight. The mixture was centrifuged (3,500 rotations per minute) at a temperature of −10° C. (3500 RPM), and the mother liquid was then poured off. The remaining solid was dissolved in hexane and refrigerated (5±3° C.) overnight. Filtration of the precipitate yielded 50 grams of pure (R)-1-octadecyl-3-trityl-glycerol. the reaction mixture was refluxed for 17 hours poured on ice (1 kilogram) transferred to a separatory funnel extracted twice with 200 ml diethyl ether The organic phase was washed consecutively with 200 ml water, twice with 100 ml dilute (1.5%) H2SO4, 200 ml water, 200 ml concentrated aqueous sodium bicarbonate The solution was then dried over anhydrous sodium sulfate the solvent was removed under reduced pressure The residue, a brown oil, was dissolved in 250 ml ethyl acetate cooled to −20° C. overnight at a temperature of −10° C. (3500 RPM) the mother liquid was then poured off The remaining solid was dissolved in hexane refrigerated (5±3° C.) overnight Filtration of the precipitate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 ml of (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol, 27 grams of powdered potassium hydroxide and 59 grams of 1-bromooctadecane were stirred in 250 ml benzene and refluxed for 6 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 200 ml. The reaction mixture was then cooled to room temperature and stirred at this temperature overnight. 200 ml water was added, the reaction mixture extracted twice with 200 ml diethyl ether, the combined organic phase was washed with 200 ml water, and the solvent was then removed under reduced pressure. The obtained residue was dissolved in 100 ml of a mixture of 90:10:5 (v/v) methanol:water:concentrated hydrochloric acid, and the resulting solution was refluxed for 1 hour, followed by cooling to room temperature and addition of 200 ml water. The product was extracted twice with 200 ml chloroform, washed consecutively with 200 ml water, 200 ml of a saturated aqueous solution of sodium carbonate, and again with 200 ml water. The solvent was then removed under reduced pressure, and the crude product was crystallized from 500 ml hexane to give 39.5 grams of pure (S)-1-octadecyl-glycerol, which was dried in a desiccator under reduced pressure with phosphorus oxide. refluxed for 6 hours while removing the water formed by azeotropic distillation the reaction mixture extracted twice with 200 ml diethyl ether the combined organic phase was washed with 200 ml water the solvent was then removed under reduced pressure The obtained residue was dissolved in 100 ml of a mixture of 90:10:5 (v/v) methanol water:concentrated hydrochloric acid, and the resulting solution was refluxed for 1 hour by cooling to room temperature addition of 200 ml water The product was extracted twice with 200 ml chloroform washed consecutively with 200 ml water, 200 ml of a saturated aqueous solution of sodium carbonate The solvent was then removed under reduced pressure the crude product was crystallized from 500 ml hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the procedure of the reference [FEBS Letters, Vol. 116, 161 (1980)], D-mannitol was used as a starting material to give 25 g of the desired compound (needles) through 1,2-isopropylidene-sn-glycerol.