Triethylamine → 2-[4-(2-hydroxyethyl)benzyl]-5-methoxyphenyl beta-D-glucopyranoside

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Reaktionsgleichung

[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][O:30]COC)=[CH:24][CH:23]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[O:1]([C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][OH:30])=[CH:26][CH:27]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 5-methoxy-2-{4-[2-(methoxymethyl-oxy)ethyl]benzyl}phenyl β-D-glucopyranoside (0.053 g) in methanol (2.3 mL) was added p-toluenesulfonic acid monohydrate (0.032 g), and the mixture was stirred at 50° C. for 3 hours. The reaction mixture was cooled to ambient temperature, triethylamine (0.5 mL) was added to the reaction mixture, and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1) to give 2-[4-(2-hydroxyethyl)benzyl]-5-methoxyphenyl β-D-glucopyranoside (0.023 g).

Aufarbeitung

temperatureThe reaction mixture was cooled to ambient temperature
customthe solvent was removed under reduced pressure
customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=6/1)

Quellen und Nachweise

ORD-Eintrag: ord-8f598a0d273844468e07433455cb463b
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07129381B2

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