Thiophenol → 1-Thiophenyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose

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Reaction Steps

Compound [2] (0.31-8.02 g, 0.68-17.7 mmol) is dissolved in 3.2-100 ml of dry dichloromethane, and thiophenol (0.15-3.9 g, 1.36-35.4 mmol) and tin tetrachloride (0.35-9.22 g, 1.36-35.4 mmol) are added and the mixture is stirred until reaction is complete. The reaction mixture is diluted and then washed with saturated sodium bicarbonate solution. The crude product compound [3] obtained in this way is purified by chromatography on silica gel with an ethyl acetate/isohexane gradient (0.27-7.14 g, 0.54-14.2 mmol, about 80%) and is dissolved in anhydrous methanol (3-90 ml) and catalytic amounts of sodium methylate (prepared from 0.002-0.05 g of sodium in 0.1-2 ml of methanol) are added. After the reaction is complete, the mixture is neutralized with an acidic ion exchanger (0.2-5 g Amberlite IR-120, H+ -form) compound [4] (0.21-5.31 g, 0.54-14.1 mmol, about 80% yield). FAB-MS: M+H+ =378. NMR data consistent with Nicolaou et al., J. Am. Chem. Soc. 112:3695 (1990)) and T. J. Caulfield, Ph.D. Dissertation, The University of Pennsylvania (1991).

Provenance & Evidence