Water → 7-O-(Triethylsilyl)-10-deacetyl Baccatin III

HRID 1650361

Reaktionsgleichung

Reaktionsgleichung von HRID 1650361
[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([OH:39])[C:5]([C@@:7]1([CH3:38])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][C@@H:8]1[OH:37])=[O:6].[CH2:40]([Si:42](Cl)([CH2:45][CH3:46])[CH2:43][CH3:44])[CH3:41].C(OCC)(=O)C.O>N1C=CC=CC=1>[CH3:41][CH2:40][Si:42]([O:37][C@@H:8]1[C@@:7]2([CH3:38])[C:5]([C@H:4]([OH:39])[C:3]3[C:15]([CH3:16])([CH3:17])[C@:14]([OH:21])([C@@H:13]([O:22][C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:24])[C@@H:12]2[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9]1)[CH2:18][C@H:19]([OH:20])[C:2]=3[CH3:1])=[O:6])([CH2:45][CH3:46])[CH2:43][CH3:44]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13819ChlorotriethylsilaneHCID 15427210-deacetylbaccatin III

Produkt 1

HCID 117349827-O-(Triethylsilyl)-10-deacetyl Baccatin IIIAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

544 mg (1 mmol) of 10-deacetylbaccatine III, dissolved in 50 cm3 of anhydrous pyridine, are introduced under an argon atmosphere into a 100-cm3 round-bottomed flask equipped with a magnetic stirrer. 3.36 cm3 (3.014 g; 20 mmol) of triethylsilyl chloride are then added. The homogeneous, yellow reaction mixture is then stirred for 24 hours at 0° C. Ethyl acetate and water are then added. After settling has taken place, the separated aqueous phase is extracted with ethyl acetate. The combined organic phases are treated with saturated aqueous copper sulphate solution until the pyridine has been completely removed. The organic phases are washed with water and then with saturated sodium chloride solution, and then dried over anhydrous sodium sulphate. After filtration and evaporation of the solvents under reduced pressure, 2.73 g of a product are obtained, and this is purified on a silica column, eluting with a dichloromethane/methanol (99:1 by volume) mixture. 512 mg (0.778 mmol) of 10-deacetyl-7-triethylsilylbaccatine III are thereby obtained, in a 78% yield, in the form of a white solid, the characteristics of which are as follows:

Aufarbeitung

  1. additionare introduced under an argon atmosphere into a 100-cm3 round-bottomed flask
  2. customequipped with a magnetic stirrer
  3. extractionthe separated aqueous phase is extracted with ethyl acetate
  4. additionThe combined organic phases are treated with saturated aqueous copper sulphate solution until the pyridine
  5. customhas been completely removed
  6. washThe organic phases are washed with water
  7. dry with materialwith saturated sodium chloride solution, and then dried over anhydrous sodium sulphate
  8. filtrationAfter filtration and evaporation of the solvents under reduced pressure, 2.73 g of a product
  9. customare obtained
  10. customthis is purified on a silica column
  11. washeluting with a dichloromethane/methanol (99:1 by volume) mixture

Quellen und Nachweise

ORD-Eintrag
ord-8c1af04dce9d4636b90a65115d578735
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04924011

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