Testosterone → 7alpha-Hydroxytestosterone

HRID 1156554

Reaktionsgleichung

Reaktionsgleichung von HRID 1156554
[O:1]=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[OH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]2[C@H:20]3[C@H:30]([CH2:31][CH2:32][C@:15]12[CH3:16])[C@:28]1([CH3:29])[C:23](=[CH:24][C:25](=[O:33])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3>CS(C)=O>[OH:1][C@@H:21]1[CH2:22][C:23]2[C@:28]([CH3:29])([CH2:27][CH2:26][C:25](=[O:33])[CH:24]=2)[C@@H:30]2[C@@H:20]1[C@H:17]1[C@@:15]([CH2:32][CH2:31]2)([CH3:16])[C@@H:14]([OH:13])[CH2:19][CH2:18]1

Komponenten

4

Edukt 2

HCID 6013TestosteroneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Produkt 1

HCID 655417alpha-Hydroxytestosterone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

100 ml of a nutrient medium, containing 1% cornsteep liquor and 1% glucose, were adjusted to pH 6.5 and, after sterilization, inoculated with the mycelium of IFO 6469. After incubation at 26.5° on the rotary shaking machine during 22 hours, 100 mg of 17β-hydroxy-4-androsten-3-one in 1 ml of dimethyl sulphoxide were added and the incubation was continued at 26.5° for a further 8 days. Thereafter, the fermentation solution was filtered, the filtrate was extracted with ethyl acetate and concentrated to a small volume and under reduced pressure. The concentrate was chromatographed on silicic acid with chloroform-acetone. There were obtained 17.9 mg of 7α,17β-dihydroxy-4-androsten-3-one.

Aufarbeitung

  1. waitthe incubation was continued at 26.5° for a further 8 days
  2. filtrationThereafter, the fermentation solution was filtered
  3. extractionthe filtrate was extracted with ethyl acetate
  4. concentrationconcentrated to a small volume and under reduced pressure
  5. customThe concentrate was chromatographed on silicic acid with chloroform-acetone

Quellen und Nachweise

ORD-Eintrag
ord-0c9df86d9a2b43699f78f9bbd7f0f374
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04336332

Verknüpfte Notizen

Wird geladen…