alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-phenylethyl)indole
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5][NH:6]2.[C:19]([O:22][C@@H:23]1[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:32][C@@H:24]1OC(=N)C(Cl)(Cl)Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([O:22][C@@H:23]1[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:32][C@H:24]1[O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:5][NH:6]2)(=[O:21])[CH3:20]Participants
Procedure
To a solution of 4-hydroxy-3-(2-phenylethyl)indole (70 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.22 g) in dichloromethane (3 mL) was added boron trifluoride-diethyl ether complex (0.081 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by preparative thin layer chromatography (eluent: n-hexane/ethyl acetate=1/1) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-phenylethyl)indole. This material was dissolved in tetrahydrofuran (1 mL)-methanol (0.5 mL). To the solution was added sodium methoxide (28% methanol solution, 0.024 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was purified by preparative thin layer chromatography (eluent: dichloromethane/methanol=5/1) to give the title compound (22 mg).
Workup
- customThe reaction mixture was purified by preparative thin layer chromatography (eluent: n-hexane/ethyl acetate=1/1)
Sources & evidence
- ORD record
- ord-a1614365e4184532b3c0e4eb1f67da48
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07566699B2
Reaction notes
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