Sodium Methoxide → 4-(beta-D-Glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]-thiophene
Reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:33]2[C:32]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][S:30][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:24][C:25]2[C:33]3[C:32]([CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:31][S:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]Participants
4
Procedure
To a suspension of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]thiophene (75 mg) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 0.025 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (42 mg).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)
Sources & evidence
- ORD record
- ord-458a8001c1874df6a3001836535ec454
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07566699B2
Reaction notes
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