1-Benzofuran-5-carbonyl chloride → 3-(Benzo[b]furan-5-yl-methyl)-4,6-dichloro-1-(beta-D-gluco-pyranosyl)indole

HRID 544894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 544894
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C@@H:12]1[O:29][C@H:28]([CH2:30][O:31]C(=O)C)[C@@H:23]([O:24]C(=O)C)[C@H:18]([O:19]C(=O)C)[C@H:13]1[O:14]C(=O)C.[O:35]1[CH:39]=[CH:38][C:37]2[CH:40]=[C:41]([C:44](Cl)=O)[CH:42]=[CH:43][C:36]1=2>>[O:35]1[CH:39]=[CH:38][C:37]2[CH:40]=[C:41]([CH2:44][C:4]3[C:8]4[C:7](=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=4[Cl:11])[N:6]([C@@H:12]4[O:29][C@H:28]([CH2:30][OH:31])[C@@H:23]([OH:24])[C@H:18]([OH:19])[C@H:13]4[OH:14])[CH:5]=3)[CH:42]=[CH:43][C:36]1=2

Komponenten

3

Edukt 2

HCID 27762681-Benzofuran-5-carbonyl chlorideHCID 671961924,6-dichloro-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-indole

Produkt 1

HCID 671968823-(Benzo[b]furan-5-yl-methyl)-4,6-dichloro-1-(beta-D-gluco-pyranosyl)indole

Versuchsvorschrift

4,6-Dichloro-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-indole obtained in Example 28-(3) and benzo[b]furan-5-carbonyl chloride were treated in a manner similar to Example 3 to give the titled compound as a colorless powder. APCI-Mass m/Z 478/480 (M+H). 1H-NMR (DMSO-d6) δ 3.20-3.50 (m, 4H), 3.59 (m, 1H), 3.67 (m, 1H), 4.34 (s, 2H), 4.55 (t, J=5.7 Hz, 1H), 5.11 (d, J=5.1 Hz, 1H), 5.16 (d, J=5.1 Hz, 1H), 5.24 (d, J=5.8 Hz, 1H), 5.46 (d, J=9.0 Hz, 1H), 6.87 (d, J=1.4 Hz, 1H), 7.11 (d, J=1.6 Hz, 1H), 7.19 (dd, J=8.5, 1.4 Hz, 1H), 7.33 (s, 1H), 7.42 (s, 1H), 7.49 (d, J=8.3 Hz, 1H), 7.73 (d, J=1.6 Hz, 1H), 7.93 (d, J=2.1H, z, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-99b7a8f2b91a4cfbae063fad7893af72
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935674B2

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