7-Deoxytaxol → HCID 10929863, Verbindung

HRID 279231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279231
[CH3:1][C:2]1[C@@H:19]([O:20]C([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:58][C:59]([CH3:61])=[O:60])[C:5]([C@@:7]1([CH3:57])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][CH2:8]1)=[O:6]>C(Cl)Cl.CO>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:58][C:59]([CH3:61])=[O:60])[C:5]([C@@:7]1([CH3:57])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][CH2:8]1)=[O:6]

Komponenten

4

Edukt 1

HCID 99189837-Deoxytaxol

Produkt 1

HCID 10929863HCID 10929863, VerbindungAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(2) To a solution of 7-deoxy paclitaxel (461 mg, 0.55 mmol) in 20 mL of methylene chloride and 0.4 mL of methanol was added Bu4NBH4 (283 mg, 1.1 mmol) and the solution stirred for 24 hours. The solution was quenched with saturated NH4Cl and extracted with ethyl acetate. The solution was dried over MgSO4 and concentrated. The residue was chromatographed over silica gel using hexane-ethyl acetate (1:1) to give 249 mg of product (79%).

Aufarbeitung

  1. customThe solution was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f4318bb2d32346678dd0684effc55fdf
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362217B1

Notizen zur Reaktion

Wird geladen…