Reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([O:7][C@@H:8]2[O:25][C@H:24]([CH2:26][O:27]C(=O)C)[C@@H:19]([O:20]C(=O)C)[C@H:14]([O:15]C(=O)C)[C@H:9]2[O:10]C(=O)C)[C:3]=1[CH2:31][C:32]1[S:33][CH:34]=[CH:35][C:36]=1C.[CH3:38][O-].[Na+].[CH2:41](O)[CH3:42]>>[C@@H:8]1([O:7][C:4]2[C:3]([CH2:31][C:32]3[CH:42]=[CH:41][C:34]([S:33][CH3:38])=[CH:35][CH:36]=3)=[C:2]([CH3:1])[NH:6][N:5]=2)[O:25][C@H:24]([CH2:26][OH:27])[C@@H:19]([OH:20])[C@H:14]([OH:15])[C@H:9]1[OH:10]Participants
4
Procedure
To a solution of 5-methyl-4-[(methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.42 g) in ethanol (5 mL) was added sodium methoxide (28% methanol solution, 0.042 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol =5/1) to give 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.23 g).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol =5/1)
Sources & evidence
- ORD record
- ord-0ef7075b44b543b6a3a66f4945f2d4d2
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189702B2
Linked notes
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