[C:1]([O:8][CH2:9][CH3:10])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=[O:5].F[C:12](F)(F)C(O)=O.[CH2:18]([N:25]([Si](C)(C)C)[CH2:26]OC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH2:9]([O:8][C:1]([C@H:2]1[C@H:3]([C:4]([OH:6])=[O:5])[CH2:26][N:25]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12]1)=[O:7])[CH3:10]To a stirred solution of mono ethyl fumarate (2.85 g, 19.8 mmol) and trifluoroacetic acid (1.98 mmol, 0.15 mL) in methylene chloride (50 mL), N-benzyl-N-(methoxymethyl)trimethylsilyl amine (Aldrich) (9.41 g, 39.6 mmol) is added at 0° C. under N2. The mixture is stirred at 0° C. for 30 min and then at RT over 48 h. The crude material is concentrated and purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 85:15 to 85:15+2% NH4OH) to give the title compound. MS (LC-MS): 278.0 [M+H]+. 1H-NMR (CD3OD, 400 MHz): δ=1.29 (t, 3H), 3.28 (m, 5H), 3.60 (m, 1 H), 4.07 (m, 2H), 4.20 (m, 2H), 7.47 (m, 5H) ppm.
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