Reaction Steps
A stirred solution of olefin 3.18 (0.115 g, 0.29 mmol) in t-BuOH (3 mL) and water (1 mL) at 0° C., containing N-methyl morpholine N-oxide (0.069 g, 0.59 mmol), was treated with 2.5% OsO4 solution (0.16 mL). The reaction mixture was brought to room temperature slowly and stirred for 12 h; Na2SO3 (200 mg) was added and, after stirring for a few more minutes, it was concentrated under suction. The residue was extracted with EtOAc (3×10 mL) and the combined extract was washed with water (1×10 mL) and dried (Na2SO4). The residue obtained after evaporation of the solvent was purified by flash column chromatography over silica gel using hexane:EtOAc (3:2) as eluant to give 3.2 (0.070 g ,63%) as white solid; m.p. 61° C. (EtOAc/hexane); IR (KBr) 3380 (OH) and 1728 (C=O) cm-1 ; 1H NMR (CDCl3) δ 0.85 (distorted t, 3H, CH3 (CH2)13), 1.10-1.40 (m, 22H, CH3 (CH2)11CH2CH2OCO), 1.60 (m, 2 H, CH3 (CH2)11CH2CH2OCO), 1.86-2.12 (m, 4 H, H-4, CH2CH2COOC14H29), 2.25-2.78 (multiplets, 4 H, H-3, CH2CH2COOC14H29), 2.90 (t, J=6.5 Hz, 1 H, OH), 3.50 (dd, J=12.1, 6.5 Hz, 1 H, CHHOH), 3.65 (dd, J=12.1, 6.5 Hz, 1 H, CHHOH), 4.05 (t, J=6.7 Hz, 2 H, CH3 (CH2)11CH2CH2OCO); 13C NMR (CDCl3) δ 14.09, 22.65, 25.85, 28.05, 28.33, 28.51, 29.15, 29.21, 29.32, 29.48, 29.55, 29.61, 30.97, 31.88, 65.16, 66.41, 87.54, 173.28, 177.03; FAB MS m/z (relative intensity) 385 (38, MH+), 171 (100, MH-C14H29OH). Anal. Calcd for C22H40O5 : C, 68.7; H, 10.49. Found: C, 68.63; H, 10.44.
