p-Anisoyl chloride → 4-Fluoro-3-(4-methoxyphenylmethyl)-1-(beta-D-glucopyranosyl)-indole
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][O:30]C(=O)C)[C@@H:22]([O:23]C(=O)C)[C@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[CH3:34][O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=O)=[CH:38][CH:37]=1>>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:40][C:39]1[CH:43]=[CH:44][C:36]([O:35][CH3:34])=[CH:37][CH:38]=1)=[CH:5][N:6]2[C@@H:11]1[O:28][C@H:27]([CH2:29][OH:30])[C@@H:22]([OH:23])[C@H:17]([OH:18])[C@H:12]1[OH:13]Participants
3
Procedure
4-Fluoro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole obtained in Example 2-(3) and 4-methoxybenzoyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 435 (M+NH4)H. 1H-NMR (DMSO-d6) δ 3.21-3.26 (m, 1H), 3.37-3.46 (m, 3H), 3.63-3.68 (m, 2H), 3.70 (s, 3H), 4.02 (s, 2H), 4.53 (t, J=5.4 Hz, 1H), 5.09 (d. J=5.3 Hz, 1H), 5.15 (d. J=5.0 Hz, 1H), 5.20 (d, J=5.9 Hz, 1H), 5.37 (d, J=9.2 Hz, 1H), 6.74 (dd, J=11.2, 7.9 Hz, 1H), 6.83 (d, J=8.5 Hz, 2H), 7.07 (td, J=8.0, 5.2 Hz, 1H), 7.17 (d, J=8.7 Hz, 2H), 7.19 (s, 1H), 7.35 (d, J=8.4 Hz, 1H).
Sources & evidence
- ORD record
- ord-0181170b746d4e4fbc80cb4d834dd0ab
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935674B2
Reaction notes
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