1,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl- → HCID 178476370, Verbindung

HRID 991157

Reaktionsgleichung

Reaktionsgleichung von HRID 991157
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@@H:28]([NH2:36])[C@H:27]([O:37][C:38](=[O:40])[CH3:39])[C@H:26]1[O:41][C:42](=[O:44])[CH3:43])(=[O:3])[CH3:2].[CH3:45][C:46]([CH:48]1[C:54](=[O:55])[CH2:53][C:52]([CH3:57])([CH3:56])[CH2:51][C:49]1=[O:50])=O>CO>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@@H:28]([NH:36][C:46](=[C:48]2[C:54](=[O:55])[CH2:53][C:52]([CH3:57])([CH3:56])[CH2:51][C:49]2=[O:50])[CH3:45])[C@H:27]([O:37][C:38](=[O:40])[CH3:39])[C@H:26]1[O:41][C:42](=[O:44])[CH3:43])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 5194481,3-Cyclohexanedione, 2-acetyl-5,5-dimethyl-HCID 233928414-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galacto-pyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl amine

Produkt 1

HCID 178476370HCID 178476370, VerbindungAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl amine (157 mg, 0.24 mmol) and 2-acetyldimedone (81 mg, 0.45 mmol) in MeOH (5 ml) was refluxed for 5 h. The reaction mixture was evaporated, and the residue was purified by chromatography using CHCl3/EtOAc 1:1 as the mobile phase, to give 4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2,3,6-tri-O-acetyl-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]-β-D-glucopyranosyl amine (27) (106 mg, 54%).

Aufarbeitung

  1. temperaturewas refluxed for 5 h
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-03524f76bd294533918f34320899892f
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462183B1

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