1,3-Diolein

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

Procedure: In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound of the invention. This reaction mixture was then filtered the filtrate was concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water The washed solution was dried concentrated

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

Procedure: To 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol was added 266 ml of 0.1 M tetra-n-butylammonium fluoride-tetrahydrofuran and the reaction was carried out at ambient temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride, washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/ethyl acetate-n-hexane) to provide 3.97 g (48.0% based on 2-O-t-butyldimethylsilylglycerol) of the title compound. After completion of the reaction the solvent was distilled off under reduced pressure the residue was diluted with methylene chloride washed with water dried concentrated

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

Procedure: In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound. This reaction mixture was then filtered the filtrate was concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water The washed solution was dried concentrated

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

Procedure: In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound. This reaction mixture was then filtered the filtrate was concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water The washed solution was dried concentrated

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

Procedure: To 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol was added 266 ml of 0.1M tetra-n-butylammonium fluoride-tetrahydrofuran and the reaction was carried out at ambient temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride, washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/ethyl acetate-n-hexane) to provide 3.97 g (48.0% based on 2-O-t-butyldimethylsilylglycerol) of the title compound. After completion of the reaction the solvent was distilled off under reduced pressure the residue was diluted with methylene chloride washed with water dried concentrated

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

Procedure: In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound of the invention. This reaction mixture was then filtered the filtrate was concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water The washed solution was dried concentrated

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

Procedure: In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound of the invention. This reaction mixture was then filtered the filtrate was concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water The washed solution was dried concentrated

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

Procedure: To 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol was added 266 ml of 0.1 M tetra-n-butylammonium fluoride-tetrahydrofuran and the reaction was carried out at ambient temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride, washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/ethyl acetate-n-hexane) to provide 3.97 g (48.0% based on 2-O-t-butyldimethylsilylglycerol) of the title compound. After completion of the reaction the solvent was distilled off under reduced pressure the residue was diluted with methylene chloride washed with water dried concentrated

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

Procedure: 3.8 g of dimeric dihydroxyacetone, 25 g of oleic acid, 20 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloric acid and 12.9 g of 4-dimethylaminopyridine were added to 150 mL of dichloromethane, and then the solution was stirred for 4 hours at room temperature. The reaction solution was mixed with 0.5 M potassium dihydrogenphosphate solution and subjected to extraction with dichloromethane, and then the extract washed with water and concentrated under reduced pressure after drying. A powder obtained by adding 1 L of methanol to the residue was collected, and then dried. The powder was dissolved in a mixture of 170 mL of tetrahydrofuran and 17 mL of acetic acid solution, and then 1.7 g of sodium borohydride was gradually added. After stirring for 2 hours at room temperature, the reaction solution was mixed with saturated sodium bicarbonate water, and then subjected to extraction with ethyl acetate. The organic layer was concentrated under reduced pressure after drying. The residue was purified with silica gel column chromatography to obtain 14.5 g of the objective compound. subjected to extraction with dichloromethane the extract washed with water concentrated under reduced pressure after drying A powder obtained was collected dried The powder was dissolved in a mixture of 170 mL of tetrahydrofuran and 17 mL of acetic acid solution 1.7 g of sodium borohydride was gradually added After stirring for 2 hours at room temperature the reaction solution was mixed with saturated sodium bicarbonate water subjected to extraction with ethyl acetate The organic layer was concentrated under reduced pressure after drying The residue was purified with silica gel column chromatography

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

Procedure: 3.8 g of dihydroxyacetone dimer, 25 g of oleic acid, g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt, and 12.9 g of 4-dimethylaminopyridine were dissolved in 150 mL of dichloromethane, for reaction under agitation at ambient temperature for 4 hours. The organic layer was washed by adding aqueous 0.5 M potassium dihydrogen phosphate solution to the reaction solution. After the organic layer was dried and concentrated under reduced pressure, 1 L of methanol was added to the resulting residue; the generated powder was filtered and recovered, and then dried. The dried powder was dissolved in a mixture solution of 170 mL of tetrahydrofuran and 17 mL of aqueous 10% acetic acid solution, to which 1.7 g of sodium borohydride was added in small portions at 0° C. Subsequently, the resulting mixture was agitated at ambient temperature for 2 hours to promote the reaction. The resulting reaction solution was poured in saturated aqueous sodium hydrogen carbonate, for extraction with ethyl acetate. After the organic layer was dried, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, to obtain 14.5 g of the intended product. The organic layer was washed by adding aqueous 0.5 M potassium dihydrogen phosphate solution to the reaction solution After the organic layer was dried concentrated under reduced pressure, 1 L of methanol was added to the resulting residue the generated powder was filtered recovered dried The dried powder was dissolved in a mixture solution of 170 mL of tetrahydrofuran and 17 mL of aqueous 10% acetic acid solution, to which 1.7 g of sodium borohydride was added in small portions at 0° C the reaction The resulting reaction solution After the organic layer was dried the organic layer was concentrated under reduced pressure The residue was purified by silica gel column chromatography

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

Procedure: In a solvent mixture of 3 ml N,N-dimethylformamide and 6 ml methylene chloride was dissolved 172 mg (0.277 mmol) of 1,3-dioleoylglycerol followed by addition of 101 mg (0.556 mmol) of N,N-diethyl-β-alanine (hydrochloride), 114 mg (0.553 mmol) of N,N-dicyclohexylcarbodiimide, and 7 mg (0.057 mmol) of 4-dimethylaminopyridine and the mixture was stirred overnight. This reaction mixture was then filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with water. The washed solution was dried and concentrated and the residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 129 mg (62%) of the title compound. This reaction mixture was then filtered the filtrate was concentrated under reduced pressure The residue was dissolved in methylene chloride washed with water The washed solution was dried concentrated

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

Procedure: To 1,3-O-dioleoyl-2-O-(t-butyldimethylsilyl)glycerol was added 266 ml of 0.1M tetra-n-butylammonium fluoride-tetrahydrofuran and the reaction was carried out at ambient temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was diluted with methylene chloride, washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/ethyl acetate-n-hexane) to provide 3.97 g (48.0% based on 2-O-t-butyldimethylsilylglycerol) of the title compound. After completion of the reaction the solvent was distilled off under reduced pressure the residue was diluted with methylene chloride washed with water dried concentrated