2-Methyl-4-nitrophenol → 2-Methyl-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

HRID 863784

Reaktionsgleichung

Reaktionsgleichung von HRID 863784
Cl[Sn](Cl)(Cl)Cl.[CH3:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[OH:16].C(O[C@@H:21]1[O:38][C@H:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]1[O:23][C:24](=[O:26])[CH3:25])(=O)C>O>[C:24]([O:23][C@@H:22]1[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[O:38][C@@H:21]1[O:16][C:8]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=1[CH3:6])(=[O:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 74422-Methyl-4-nitrophenolHCID 24287Tin tetrachlorideHCID 94752beta-D-Galactose pentaacetate

Produkt 1

HCID 538308232-Methyl-4-nitrophenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

SnCl4 (0.6 ml) is added slowly to a solution of 2-methyl-4-nitrophenol (ref.: J. S. ANDERSON and K. C. BROWN, Synthetic Commun., 13, 233-236, 1983) and 1,2,3,4,6-penta-O-acetyl-β-D-galactose (1 g, 2.56 mmol), kept at room temperature. The reaction mixture is then stirred under nitrogen for 12 hours at 60° C. After hydrolysis in iced water, extraction with CH2Cl2, followed by washing with a saturated solution of sodium bicarbonate and then water, gives 42, which is then purified by chromatography on silica gel (yield=45%).

Aufarbeitung

  1. customkept at room temperature
  2. extractionextraction with CH2Cl2
  3. washby washing with a saturated solution of sodium bicarbonate

Quellen und Nachweise

ORD-Eintrag
ord-554acb8ff6344725a459e7993f4f401c
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05561119

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