2-(4-Methoxybenzyl)phenol → 2-(4-methoxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

HRID 2375141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2375141
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])=[CH:5][CH:4]=1.[C:17]([O:20][C@@H:21]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:32]([O:38][C:39](=[O:41])[CH3:40])[C@@H:31]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[O:30][C@@H:22]1OC(=N)C(Cl)(Cl)Cl)(=[O:19])[CH3:18]>ClCCl>[C:17]([O:20][C@@H:21]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:32]([O:38][C:39](=[O:41])[CH3:40])[C@@H:31]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[O:30][C@H:22]1[O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][C:6]1[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 2584512-(4-Methoxybenzyl)phenolHCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)

Produkt 1

HCID 120199842-(4-methoxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosideAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-methoxybenzyl)phenol (46 mg) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.13 g) in dichloromethane (2 mL) was added boron trifluoride diethyl ether complex (0.033 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: dichloromethane) to give 2-(4-methoxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.11 g).

Aufarbeitung

  1. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-1f9951b7d6784793bc3c701cd1cd25b3
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465712B2

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