Toluene → 4-(1H-Imidazol-1-yl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907070

Reaktionsgleichung

Reaktionsgleichung von HRID 907070
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1Br)(=[O:3])[CH3:2].[N:20]1([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)[CH:24]=[CH:23][N:22]=[CH:21]1.C1(C)C=CC=CC=1>[Cl-].[Zn+2].[Cl-].[O-2].[Zn+2].C(#N)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:31][C:28]1[CH:27]=[CH:26][C:25]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)=[CH:30][CH:29]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 823151-(p-Hydroxyphenyl)imidazoleHCID 10948230(2S,3R,4S,5S)-2-bromotetrahydro-2H-thiopyran-3,4,5-triyl triacetate

Produkt 1

HCID 673982604-(1H-Imidazol-1-yl)phenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 3007857Zinc OxideKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 3 g (22 mmol) of zinc chloride, 5 g of 4 Å molecular sieve, 6.5 g of zinc oxide, 9 g (25 mmol) of 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl bromide, 3.2 g (20 mmol) of 4-(1H-imidazol-1-yl)phenol, 70 ml of toluene and 70 ml of acetonitrile is prepared. The mixture is kept stirred at 55° C. for 24 hours and then cooled and filtered. The residual solid is rinsed on the filter with ethyl acetate and the combined filtrates are successively washed with water, with an N sodium hydroxide solution and again with water to neutral pH. The organic phase is subsequently dried over magnesium sulfate and concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel, elution being carried out using an ethyl acetate/ethyl ether mixture (8/5; v/v). The expected compound is thus obtained in the form of a pulverulent solid which is reacted further in order to obtain the nonacetylated xyloside.

Aufarbeitung

  1. customis prepared
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe residual solid is rinsed on the
  5. filtrationfilter with ethyl acetate
  6. washthe combined filtrates are successively washed with water, with an N sodium hydroxide solution and again with water to neutral pH
  7. dry with materialThe organic phase is subsequently dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product obtained
  10. customis purified by chromatography on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-09b63d1f9cc74f4881968606780d41b6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013010B2

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