Dichloromethane → HCID 86583674, Verbindung

HRID 843504

Reaktionsgleichung

Reaktionsgleichung von HRID 843504
[C:1]([O:4][C@@H:5]1[O:27][C@H:26]([CH2:28][O:29]C(=O)C2C=CC=CC=2)[C@@H:16]([O:17]C(=O)C2C=CC=CC=2)[C@H:6]1[O:7]C(=O)C1C=CC=CC=1)(=O)[CH3:2].[F:38][C:39]([F:51])([F:50])[C:40]([NH:42][C:43]1[CH:44]=C(O)C=[CH:47][CH:48]=1)=[O:41].B(F)(F)F.ClCCl>O1CCCC1>[O:4]([C:1]1[CH:2]=[CH:47][CH:48]=[C:43]([NH:42][C:40](=[O:41])[C:39]([F:51])([F:38])[F:50])[CH:44]=1)[C@@H:5]1[O:27][C@H:26]([CH2:28][OH:29])[C@@H:16]([OH:17])[C@H:6]1[OH:7]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 6356Boron trifluorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 235054192,2,2-Trifluoro-N-(3-hydroxyphenyl)acetamide

Produkt 1

HCID 86583674HCID 86583674, VerbindungAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (500 mg, 0.99 mmol), 3-trifluoroacetamidophenol (407 mg, 1.98 mmol) from Stage 1 and boron trifluoride diethyletherate (1.41 g, 9.93 mmol, 1.25 ml) in a mixture of dry dichloromethane (10 ml) and dry tetrahydrofuran (30 ml) was stirred at room temperature under argon for 7 days. Work-up as in Stage 1 of Example 1 and purification by flash chromatography on silica gel (2% acetone in toluene as eluant) gave the title compound as a colourless solid (166 mg, 21%).

Aufarbeitung

  1. customWork-up as in Stage 1 of Example 1 and purification by flash chromatography on silica gel (2% acetone in toluene as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-3114df0bd589425ebb62cd2d20e8e0d2
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06379911B2

Verknüpfte Notizen

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