Reaction Steps
To a solution of 3-O-benzyl-1-O-oleyl-2-O-palmitoyl-sn-glycerol (110 mg, 0.16 mmol) in 2 mL CH2Cl2 at −78° C., boron trichloride (0.35 mL, 0.35 mmol) (1 M in CH2Cl2) was added over a period of 15 min. The reaction was stirred for 30 min under argon. The contents of the flask were then poured over ice water, the aqueous layer separated and extracted with CH2Cl2 (10 mL×3), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified using silica gel column chromatography (hexane:EtOAc=19:1˜7:1 (Rf=0.35) gradient) to get the alcohol (66 mg, 69%) as colorless oil. [α]D27 −3° (C=1.1, CHCl3); IR(CHCl3) cm−1 3442, 2911, 2853, 1736, 1652, 1460, 1374, 1239, 1167, 1116, 1094, 1053, 722, 700 cm−1; 1H NMR (600 MHz, CDCl3) δ 0.88 (t, J=7.2 Hz, 6H, CH3), 1.22-1.36 (m, 44 H, CH2), 1.52 (dt, J=7.2, 14.4 Hz, 4H, CH2), 1.94 (dd, J=6.0, 12.0 Hz, 4H, CH2), 2.05 (s, 1H, OH), 2.20 (t, J=7.8 Hz, 2H, CH2), 2.24 (t, J=7.8 Hz, 2H, CH2), 3.72 (s, 2H, CH2OH), 4.25 (dd, J=6.0, 12.0 Hz, 1H, CH2O Acyl), 4.31 (dd, J=4.8, 12.0 Hz, 1H, CH2OAcyl), 4.00-4.06 (dt, J=4.8, 10.2 Hz, 1H, CH), 5.35 (ddd, J=6.0, 10.8, 16.2 Hz, 2H, CH═CH); 13C NMR (150 MHz, CDCl3) δ 14.1, 22.66, 22.67, 24.78, 24.82, 24.84, 24.91, 27.14, 27.19, 29.06, 29.08, 29.15, 29.25, 29.30, 29.46, 29.50, 29.60, 29.63, 29.66, 29.67, 29.71, 29.74, 31.83, 31.88, 31.90, 34.1, 34.3, 61.5, 62.0, 72.1, 129.7, 130.0, 173.4, 173.8; EMSI calc'd for C37H70NaO5 [M+Na]+ 617.51. found: 617.60.
