Sodium Hydroxide → 5-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl beta-D-glucopyranoside

HRID 1826653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1826653
C([O:4][C@@H:5]1[C@@H:32]([O:33]C(=O)C)[C@H:31]([O:37]C(=O)C)[C@@H:30]([CH2:41][O:42]C(=O)C)[O:29][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=1)(=O)C.[OH-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=1)[C@@H:6]1[O:29][C@H:30]([CH2:41][OH:42])[C@@H:31]([OH:37])[C@H:32]([OH:33])[C@H:5]1[OH:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 12085609HCID 12085609, Verbindung

Produkt 1

HCID 688708525-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl beta-D-glucopyranosideAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.13 g) in methanol (8 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.50 mL), and the mixture was stirred at room temperature for 25 minutes. The solvent was removed under reduced pressure, and the residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=7/1) to give 5-methoxy-2-{4-[2-(methoxymethyloxy)ethyl]benzyl}phenyl β-D-glucopyranoside (0.053 g).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=7/1)

Quellen und Nachweise

ORD-Eintrag
ord-71a59695988a4491972bb4302987b785
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053060B2

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