[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH2:32]C1C=CC(OS(C(F)(F)F)(=O)=O)=CC=1.C(N([CH2:52][CH3:53])CC)C.CN(C)[CH:56]=[O:57].[CH2:59](OC)[C:60]#[CH:61]>C(OCC)(=O)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH:32]([C:52]#[CH:53])[C:60]1[CH:61]=[CH:4][C:3]([CH2:32][O:57][CH3:56])=[CH:2][CH:59]=11 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(trifluoromethylsulfonyloxy)-benzyl]-benzene, 2 mL triethylamine and 3 mL dimethylformamide are placed in a flask under argon atmosphere. 56 mg copper iodide, 103 mg bis-(triphenylphosphine)-palladium dichloride and finally 0.31 g methyl propargyl ether are added. The flask is tightly sealed and the mixture is stirred at 65° C. for 30 h. Then the reaction mixture is diluted with ethyl acetate and washed with 1 M hydrochloric acid. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1->2:1).
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