tert-Butyldimethylsilyl chloride → 1-O-benzyl-3-O-t-butyldimethylsilylglycerol

참여 물질

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1-O-Oleoyl-2-O-methyl-rac-glycerol (Compound 44) To a mixture of 1-O-benzyl-glycerol (27 mL, 0.16 mol) and t-butyldimethylsilyl chloride (25 g, 0.17 mol) in dry CH2Cl2 (250 mL) under N2 was added DMAP (0.8 g, 6.6 mmol) followed by the addition of TEA (23 ml, 0.17 mol). After 3 hours, the mixture was washed with H2O (2×100 mL), dried (MgSO4) and concentrated to give 1-O-benzyl-3-O-t-butyldimethylsilyl-rac-glycerol (40) (48.8 g, 100%) as a yellow oil. 1H NMR (360 MHz; CDCl3): (0.06 (6H, s, Me2Si), 0.89 (9H, s, ButSi), 3.48-3.56 (2H, m, 1-H2 or 3-H2), 3.64 (1H, dd, J 10 and 5.5 Hz, 1-H or 3-H), 3.68 (1H, dd, J 10 and 5 Hz, 1-H or 3-H), 3.86 (1H, quintet, J 5.5 Hz, 2-H), 4.56 (2H, s, —OCH2Ph) and 7.27-7.35 (5H, m, —Ph).

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