Sodium Bicarbonate → HCID 12085609, Verbindung

HRID 1982833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982833
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22])=[CH:13][CH:12]=2)=[C:7]([OH:9])[CH:8]=1.[C:23]([O:26][C@@H:27]1[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:38]([O:44][C:45](=[O:47])[CH3:46])[C@@H:37]([CH2:48][O:49][C:50](=[O:52])[CH3:51])[O:36][C@@H:28]1OC(=N)C(Cl)(Cl)Cl)(=[O:25])[CH3:24].C(=O)([O-])O.[Na+]>ClCCl>[C:23]([O:26][C@@H:27]1[C@@H:39]([O:40][C:41](=[O:43])[CH3:42])[C@H:38]([O:44][C:45](=[O:47])[CH3:46])[C@@H:37]([CH2:48][O:49][C:50](=[O:52])[CH3:51])[O:36][C@H:28]1[O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19][CH2:20][O:21][CH3:22])=[CH:13][CH:12]=1)(=[O:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 120855965-Methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenol

Produkt 1

HCID 12085609HCID 12085609, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenol (0.19 g) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.40 g) in dichloromethane (15 mL) was added boron trifluoride diethyl ether complex (0.088 mL), and the mixture was stirred for 20 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate, and the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give 5-methoxy-2-{4-[2-(methoxymethyloxy)ethyl]-benzyl}phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.33 g).

Aufarbeitung

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-f1d7b84f66c34cfc9425ee6f4a9e0a7e
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541341B2

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