Ethanethiol → 2-(beta-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene

HRID 15412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15412
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[S:44][C:43]2[C:45]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=3)=[CH:46][CH:47]=[CH:48][C:42]=2[CH:41]=1)C1C=CC=CC=1.C(S)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C@@H:10]1([C:40]2[S:44][C:43]3[C:45]([CH2:49][C:50]4[CH:51]=[CH:52][C:53]([CH3:56])=[CH:54][CH:55]=4)=[CH:46][CH:47]=[CH:48][C:42]=3[CH:41]=2)[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]1[OH:8]

Komponenten

5

Edukt 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 68714543HCID 68714543, Verbindung

Produkt 1

HCID 117499522-(beta-D-Glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiopheneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-7-(4-methylbenzyl)benzo[b]thiophene (0.95 g) and ethanethiol (1.8 mL) in dichloromethane (15 mL) was added boron trifluoride diethyl ether complex (2.1 mL) at room temperature. The reaction mixture was stirred at room temperature for 3 hours, and a saturated potassium carbonate aqueous solution was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.16 g).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-a0615df7fb9943238736a4156d6b0da8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732596B2

Notizen zur Reaktion

Wird geladen…