C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]1([CH3:28])[O:25][CH:24]([CH2:26][OH:27])[CH2:23][O:22]1.O[C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:20][C:21]1([CH3:28])[O:25][CH:24]([CH2:26][O:27][C:30]2[CH:37]=[CH:36][C:33]([CH:34]=[O:35])=[CH:32][CH:31]=2)[CH2:23][O:22]139.3 g (150 mmol) of triphenylphosphine are added to a solution of 13.2 g (100 mmol) of 1,2-O-isopropylideneglycerol in 250 ml of dry THF, and the mixture is stirred at RT for 30 min. The mixture is cooled to about 0° C., and 12.2 g (100 mmol) of 4-hydroxybenzaldehyde and 31.9 g (150 mmol) of diisopropyl azodicarboxylate (DIAD) are added. The yellow reaction solution is stirred at RT for 16 h. The mixture is then concentrated using a rotary evaporator, and the residue is added to 150 ml of sat. sodium bicarbonate solution. The mixture is extracted with ethyl acetate (three times, 150 ml each), and the combined organic phases are dried over sodium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase gradient cyclohexane→cyclohexane/ethyl acetate 2:1).
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