반응 #217183

반응 방정식

compound [ 2 ]

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

thiophenol

tin tetrachloride

→

compound [ 3 ]

수율 99.0%

1-Thiophenyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

수율 99.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONThe reaction mixture is diluted
2. 2
   세척washed with saturated sodium bicarbonate solution

실험 절차

The product 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 acetic ion exchanger (0.2-5 g Amberlite IR-120, H+ -form) (compound [5]; 0.21-5.31 g, 0.54-14.1 mmol, about 99% 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).

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