반응 #217181

반응 방정식

compound [ 2 ]

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

thiophenol

tin tetrachloride

→

compound [ 3 ]

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

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONThe reaction mixture is diluted
2. 2
   세척washed with saturated sodium bicarbonate solution
3. 3
   농축Concentration

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. Concentration results in the crude product compound [3]. Purification takes place by chromatography on silica gel with an ethyl acetate/isohexane gradient (0.27-71.4 g, 0.54-14.2 mmol, about 80%). FAB-MS: M+H+ =504. 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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