Reaktionsgleichung
B(F)(F)F.CCOCC.Cl[C:11](Cl)(Cl)[C:12](=N)[O:13][C@H:14]1[S:31][CH2:30][C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]1[O:16][C:17](=[O:19])[CH3:18].OC1C=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:17]([O:16][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[CH2:30][S:31][C@H:14]1[O:13][C:12]1[CH:37]=[CH:38][C:39]([C:40]#[N:41])=[CH:42][CH:11]=1)(=[O:19])[CH3:18]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
1 ml of a 0.1M solution of boron trifluoride etherate in methylene chloride is added at -15° C., under an inert atmosphere, to a suspension of 250 mg (0.57.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 57 mg (0.48.10-3 mol) of 4-hydroxybenzonitrile and a molecular sieve (1 nm) in 10 ml of methylene chloride. The reaction medium is allowed to return gradually to 0° C. and, after a reaction time of 3 h, is neutralized with sodium bicarbonate. The reaction mixture is then washed with water and dried over magnesium sulfate, MgSO4, and the solvent is evaporated off under reduced pressure. 150 mg (yield: 80%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent.
Aufarbeitung
- customto return gradually to 0° C.
- customafter a reaction time of 3 h
- washThe reaction mixture is then washed with water
- dry with materialdried over magnesium sulfate, MgSO4
- customthe solvent is evaporated off under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-418881fc22e24d458e9e207dc7692320
- Quelldatensatz
- uspto-grants-1993_09
- Patentnummer
- US05246961
Verknüpfte Notizen
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