[Si:1]([O:8][C@@H:9]1[CH2:13][C:12](=O)[CH:11]2[O:15][CH:10]12)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[SH:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(N(CC)CC)C.[Cl-].[NH4+]>CO>[Si:1]([O:8][CH:9]1[CH2:10][C:11](=[O:15])[C:12]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]
2.80 g (12.2 mmoles) of 4(R)-t-butyldimethylsilyloxy-2,3-epoxycyclopentanone and 1.30 g (12.2 mmoles) of 4-mercaptobutan-1-ol were dissolved in 12 ml of methanol, and with stirring 1.87 ml (13.5 mmoles) of triethylamine was added. The stirring was continued for 30 minutes. Ten milliliters of a saturated aqueous solution of ammonium chloride was added, and the mixture was concentrated. The residue was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting oily product was chromatographed on a silica gel column using hexane/ethyl acetate (8/1) as an eluent to give 3.12 g (81%) of 4(RS)-t-butyldimethylsilyloxy-2-(4-hydroxybutylthio)-2-cyclopentenone.
Loading…
