diethyl 2,2,16,16-tetramethyl-9-oxoheptadecanedioate

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

Procedure: Under N2-atmosphere, methyl tert-butyl ether (MTBE, 80 mL) was added to LiAlH4 (0.67 g, 17.65 mmol) and the suspension was stirred under cooling with an ice-water bath. A solution of 209i (3.0 g, 7.03 mmol) in MTBE (20 mL) was added dropwise, followed by additional MTBE (40 mL). After 2 h at 0° C., the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) and allowed to warm to room temperature overnight. The mixture was cooled with an ice-water bath and carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL). The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) and the solution was stirred at room temperature for 15 min. The layers were separated and the aqueous layer was extracted with MTBE (40 mL). The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL), dried over anhydrous MgSO4, concentrated in vacuo and dried in high vacuo. The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL). The crystals were filtered, washed with ice-cold CH2Cl2 (20 mL) and dried in high vacuo to furnish 211i (1.59 g, 66%) as a white solid. Mp 75-77° C. 1H NMR (CDCl3): δ (ppm): 3.57 (m, 1 H), 3.30 (s, 4 H), 1.72 (br, 2 H), 1.50-1.16 (m, 25 H), 0.85 (s, 12 H). 13C NMR (CDCl3): δ (ppm): 72.09, 38.79, 37.61, 35.21, 30.70, 29.85, 25.78, 24.06, 23.92. HRMS (LSIMS, gly): Calcd for C21H45O3 (MEP): 345.3369, found: 345.3364. HPLC: 95.0% pure. under cooling with an ice-water bath the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) The mixture was cooled with an ice-water bath carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL) The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) the solution was stirred at room temperature for 15 min The layers were separated the aqueous layer was extracted with MTBE (40 mL) The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL) dried over anhydrous MgSO4 concentrated in vacuo dried in high vacuo The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL) The crystals were filtered washed with ice-cold CH2Cl2 (20 mL) dried in high vacuo

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

Procedure: To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added coned HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): 8 (ppm): 4.14 (q, J=7.1, 4 H), 2.41 (t, J=7.0, 4 H), 1.66-1.45 (m, 8 H), 1.35-1.20 (m, 12 H), 1.25 (t, J=7.1, 6 H), 1.17 (s, 12 H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423, found: 427.3430. The layers were separated the aqueous layer was extracted with CH2Cl2 (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) dried over anhydrous MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

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

Procedure: Under N2-atmosphere, methyl tert-butyl ether (MTBE, 80 mL) was added to LiAlH4 (0.67 g, 17.65 mmol) and the suspension was stirred under cooling with an ice-water bath. A solution of 209i (3.0 g, 7.03 mmol) in MTBE (20 mL) was added dropwise, followed by additional MTBE (40 mL). After 2 h at 0° C., the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) and allowed to warm to room temperature overnight. The mixture was cooled with an ice-water bath and carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL). The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) and the solution was stirred at room temperature for 15 min. The layers were separated and the aqueous layer was extracted with MTBE (40 mL). The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL), dried over anhydrous MgSO4, concentrated in vacuo and dried in high vacuo. The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL). The crystals were filtered, washed with ice-cold CH2Cl2 (20 mL) and dried in high vacuo to furnish 211i (1.59 g, 66%) as a white solid. Mp 75-77° C. 1H NMR (CDCl3): δ (ppm): 3.57 (m, 1H), 3.30 (s, 4H), 1.72 (br, 2H), 1.50-1.16 (m, 25H), 0.85 (s, 12H). 13C NMR (CDCl3): δ (ppm): 72.09, 38.79, 37.61, 35.21, 30.70, 29.85, 25.78, 24.06, 23.92. HRMS (LSIMS, gly): Calcd for C21H45O3 (MH+): 345.3369, found: 345.3364. HPLC: 95.0% pure. under cooling with an ice-water bath the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) The mixture was cooled with an ice-water bath carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL) The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) the solution was stirred at room temperature for 15 min The layers were separated the aqueous layer was extracted with MTBE (40 mL) The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL) dried over anhydrous MgSO4 concentrated in vacuo dried in high vacuo The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL) The crystals were filtered washed with ice-cold CH2Cl2 (20 mL) dried in high vacuo

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

Procedure: To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added concd HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): δ (ppm): 4.14 (q, J=7.1, 4H), 2.41 (t, J=7.0, 4H), 1.66-1.45 (m, 8H), 1.35-1.20 (m, 12H), 1.25 (t, J=7.1, 6H), 1.17 (s, 12H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423, found: 427.3430. The layers were separated the aqueous layer was extracted with CH2Cl2 (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) dried over anhydrous MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

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

Procedure: Under N2-atmosphere, methyl tert-butyl ether (MTBE, 80 mL) was added to LiAlH4 (0.67 g, 17.65 mmol) and the suspension was stirred under cooling with an ice-water bath. A solution of 209i (3.0 g, 7.03 mmol) in MTBE (20 mL) was added dropwise, followed by additional MTBE (40 mL). After 2 h at 0° C., the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) and allowed to warm to room temperature overnight. The mixture was cooled with an ice-water bath and carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL). The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) and the solution was stirred at room temperature for 15 min. The layers were separated and the aqueous layer was extracted with MTBE (40 mL). The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL), dried over anhydrous MgSO4, concentrated in vacuo and dried in high vacuo. The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL). The crystals were filtered, washed with ice-cold CH2Cl2 (20 mL) and dried in high vacuo to furnish 211i (1.59 g, 66%) as a white solid. Mp 75-77° C. 1H NMR (CDCl3): δ (ppm): 3.57 (m, 1H), 3.30 (s, 4H), 1.72 (br, 2H), 1.50-1.16 (m, 25H), 0.85 (s, 12H). 13C NMR (CDCl3): δ (ppm): 72.09, 38.79, 37.61, 35.21, 30.70, 29.85, 25.78, 24.06, 23.92. HRMS (LSIMS, gly): Calcd for C21H45O3 (MH+): 345.3369, found: 345.3364. HPLC: 95.0% pure. under cooling with an ice-water bath the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) The mixture was cooled with an ice-water bath carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL) The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) the solution was stirred at room temperature for 15 min The layers were separated the aqueous layer was extracted with MTBE (40 mL) The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL) dried over anhydrous MgSO4 concentrated in vacuo dried in high vacuo The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL) The crystals were filtered washed with ice-cold CH2Cl2 (20 mL) dried in high vacuo

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

Procedure: To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added coned HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): δ (ppm): 4.14 (q, J=7.1, 4H), 2.41 (t, J=7.0, 4 H), 1.66-1.45 (m, 8H), 1.35-1.20 (m, 12H), 1.25 (t, J=7.1, 6 H), 1.17 (s, 12H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423, found: 427.3430. The layers were separated the aqueous layer was extracted with CH2Cl2 (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) dried over anhydrous MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

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

Procedure: Under N2-atmosphere, methyl tert-butyl ether (MTBE, 80 mL) was added to LiAlH4 (0.67 g, 17.65 mmol) and the suspension was stirred under cooling with an ice-water bath. A solution of 209i (3.0 g, 7.03 mmol) in MTBE (20 mL) was added dropwise, followed by additional MTBE (40 mL). After 2 h at 0° C., the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) and allowed to warm to room temperature overnight. The mixture was cooled with an ice-water bath and carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL). The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) and the solution was stirred at room temperature for 15 min. The layers were separated and the aqueous layer was extracted with MTBE (40 mL). The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL), dried over anhydrous MgSO4, concentrated in vacuo and dried in high vacuo. The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL). The crystals were filtered, washed with ice-cold CH2Cl2 (20 mL) and dried in high vacuo to furnish 211i (1.59 g, 66%) as a white solid. Mp 75-77° C. 1H NMR (CDCl3): δ (ppm): 3.57 (m, 1H), 3.30 (s, 4H), 1.72 (br, 2H), 1.50-1.16 (m, 25H), 0.85 (s, 12H). 13C NMR (CDCl3): δ (ppm): 72.09, 38.79, 37.61, 35.21, 30.70, 29.85, 25.78, 24.06, 23.92. HRMS (LSIMS, gly): Calcd for C21H45O3 (MH+): 345.3369. found: 345.3364. HPLC: 95.0% pure. under cooling with an ice-water bath the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL) The mixture was cooled with an ice-water bath carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL) The pH was adjusted to 1 by addition of 2 N aqueous sulfuric acid (28 mL) the solution was stirred at room temperature for 15 min The layers were separated the aqueous layer was extracted with MTBE (40 mL) The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), and brine (40 mL) dried over anhydrous MgSO4 concentrated in vacuo dried in high vacuo The crude product (2.65 g) was purified by recrystallization from hot CH2Cl2 (20 mL) The crystals were filtered washed with ice-cold CH2Cl2 (20 mL) dried in high vacuo

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

Procedure: To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added coned HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): δ (ppm): 4.14 (q, J=7.1, 4H), 2.41 (t, J=7.0, 4H), 1.66-1.45 (m, 8H), 1.35-1.20 (m, 12H), 1.25 (t, J=7.1, 6H), 1.17 (s, 12H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (ME): 427.3423. found: 427.3430. The layers were separated the aqueous layer was extracted with CH2Cl2 (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) dried over anhydrous MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

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

Procedure: To a solution of 208i (12.0 g, 20.3 mmol) in CH2Cl2 (200 mL) was added concd HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature and diluted with water (200 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 209i (3.5 g, 40.0%) as a colorless oil. 1H NMR (CDCl3): δ (ppm): 4.14 (q, J=7.1, 4H), 2.41 (t, J=7.0, 4H), 1.66-1.45 (m, 8H), 1.35-1.20 (m, 12H), 1.25 (t, J=7.1, 6H), 1.17 (s, 12H). 13C NMR (CDCl3): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423, found: 427.3430. The layers were separated the aqueous layer was extracted with CH2Cl2 (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) dried over anhydrous MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under N2-atmosphere, methyl tert-butyl ether (MTBE, 80 mL) was added to lithium aluminum hydride (0.67 g, 17.60 mmol) and the suspension was stirred under cooling with an ice-water bath (0° C.). A solution of 2,2,16,16-tetramethyl-9-oxoheptadecanedioic acid diethyl ester (3.0 g, 7.04 mmol) in MTBE (20 mL) was added dropwise, followed by additional MTBE (40 mL). After 2 h at 0° C., the reaction mixture was carefully quenched by addition of ethyl acetate (8 mL, 80 mmol) and allowed to warm to room temperature overnight. The mixture was cooled with an ice-water bath and carefully hydrolyzed by addition of crushed ice (15 g) and water (15 mL). The pH was adjusted to 1 by addition of 2 N sulfuric acid (28 mL) and the solution was stirred at room temperature for 15 min. The layers were separated and the aqueous layer was extracted with MTBE (40 mL). The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), brine (40 mL), dried over MgSO4, concentrated in vacuo and dried in high vacuo to yield a crude product (2.65 g). The crude product was purified by recrystallization from hot CH2Cl2 (20 mL), which was cooled to room temperature and then kept at −5° C. The crystals were filtered, washed with ice-cold CH2Cl2 (20 mL) and dried in high vacuo. This process was repeated to furnish 2,2,16,16-tetramethylheptadecane-1,9,17-triol (1.59 g, 65%) as a white solid. Mp 75-77° C. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 3.57 (m, 1H), 3.30 (s, 4H), 1.72 (br, 2H), 1.50-1.16 (m, 25H), 0.85 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 72.09, 38.79, 37.61, 35.21, 30.70, 29.85, 25.78, 24.06, 23.92. HRMS (LSIMS, gly): Calcd for C21H45O3 (MH+): 345.3369. found: 345.3364. HPLC: 95% pure. to warm to room temperature overnight The mixture was cooled with an ice-water bath the solution was stirred at room temperature for 15 min The layers were separated the aqueous layer was extracted with MTBE (40 mL) The combined organic layers were washed with deionized water (50 mL), saturated NaHCO3 solution (40 mL), brine (40 mL) dried over MgSO4 concentrated in vacuo dried in high vacuo to yield a crude product (2.65 g) The crude product was purified by recrystallization from hot CH2Cl2 (20 mL), which was cooled to room temperature kept at −5° C The crystals were filtered washed with ice-cold CH2Cl2 (20 mL) dried in high vacuo

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

Procedure: To a solution of 9-isocyano-2,2,16,16-tetramethyl-9-(toluene-4-sulfonyl)-heptadecanedioic acid diethyl ester (12.0 g, 20.3 mmol) in methylene chloride (200 mL) was added concd HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature. The mixture was diluted with water (200 mL), the layers were separated, and the aqueous layer was extracted with methylene chloride (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL). The solution was dried over MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 2,2,16,16-tetramethyl-9-oxoheptadecanedioic acid diethyl ester (3.5 g, 40%) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.14 (q, J=7.1 Hz, 4H), 2.41 (t, J=7.0 Hz, 4H), 1.66-1.35 (m, 20H), 1.25 (t, J=7.1 Hz, 6H), 1.17 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423. found: 427.3430. the layers were separated the aqueous layer was extracted with methylene chloride (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) The solution was dried over MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)

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

Procedure: To a solution of 9-isocyano-2,2,16,16-tetramethyl-9-(toluene-4-sulfonyl)-heptadecanedioic acid diethyl ester (12.0 g, 20.3 mmol) in methylene chloride (200 mL) was added concd HCl (47 mL). The reaction mixture was stirred for 80 min at room temperature. The mixture was diluted with water (200 mL), the layers were separated, and the aqueous layer was extracted with methylene chloride (3×70 mL). The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL). The solution was dried over MgSO4, and concentrated in vacuo to yield the crude product (7.52 g). Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9) gave 2,2,16,16-tetramethyl-9-oxoheptadecanedioic acid diethyl ester (3.5 g, 40%) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 4.14 (q, J=7.1 Hz, 4H), 2.41 (t, J=7.0 Hz, 4H), 1.66-1.35 (m, 20H), 1.25 (t, J=7.1 Hz, 6H), 1.17 (s, 12H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 211.24, 177.89, 60.01, 42.69, 42.07, 40.64, 29.86, 29.07, 25.13, 24.73, 23.74, 14.24. HRMS (LSIMS, gly): Calcd for C25H47O5 (MH+): 427.3423. found: 427.3430. the layers were separated the aqueous layer was extracted with methylene chloride (3×70 mL) The combined organic layers were washed with saturated NaHCO3 solution (3×40 mL) and brine (50 mL) The solution was dried over MgSO4 concentrated in vacuo to yield the crude product (7.52 g) Purification by column chromatography (silica gel, ethyl acetate/hexanes=1/9)