Reaction Steps
A solution of 2.14 (0.024 g, 0.1 mmol) in CH2Cl2 (5 mL) was stirred with pyridine (0.032 mL, 0.4 mmol), a catalytic amount of dimethylaminopyridine, and tetradecanoyl chloride (0.054 mL, 0.2 mmol) for 2 h at room temperature. The solution was concentrated and the residue was purified by flash column chromatography over silica gel with hexane:EtOAc (2:1) as eluant to give 2.15 (0.041 g, 92%) as an oil; [α]22D +1.43° (c 4.2, CHCl3); IR (neat) 1783 and 1743 cm-1 (C=O); 1H NMR (CDCl3) δ 0.85 (distorted triplet, 3 H, CH3), 1.10-1.40 (m, 20 H, CH3 (CH2)10CH2CH2CO), 1.60 (br m, 2 H, CH3 (CH2)10CH2CH2CO), 2.00-2.30 (m, 2 H, H-4), 2.30 (t, J=7.5 Hz, 2 H, CH3 (CH2)10CH2CH2CO), 2.50-2.75 (m, 2 H, H-3), 3.60 (br s, 2 H, CH2OCH2Ph), 4.20 (AB q, J=11.9 Hz, 2 H, CH2OCO), 4.55 (br s, 2 H, CH2OCH2Ph), 7.20-7.40 (m, 5 H, Ph); 13C NMR (CDCl3) δ 14.09, 22.65, 24.81, 26.40, 28.78, 29.07, 29.20, 29.32, 29.42, 29.57, 29.61, 29.64, 31.89, 34.03, 65.99, 72.21, 73.76, 84.94, 127.63, 127.93, 128.49, 137.33, 173.14, 176.30. Anal. Calcd for C27H42O5 : C, 72.61; H, 9.48. Found: C, 72.70; H, 9.50.
