Sodium Methoxide → 4-(beta-D-Glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]-thiophene

HRID 230887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230887
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:33]2[C:32]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][S:30][C:29]=2[CH:28]=[CH:27][CH:26]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:24][C:25]2[C:33]3[C:32]([CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:31][S:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 671360454-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]thiophene

Produkt 1

HCID 671362524-(beta-D-Glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]-thiopheneAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]thiophene (75 mg) in methanol (3 mL) was added sodium methoxide (28% methanol solution, 0.025 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (42 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-458a8001c1874df6a3001836535ec454
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

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