Disodium → (24R)-5,7-cholestadiene-3beta,24,25-triol 3-tetrahydropyranyl ether

HRID 67048

Reaktionsgleichung

Reaktionsgleichung von HRID 67048
[Na][Na].[O:3]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C@H:10]2[CH2:45][CH2:44][C@@:43]3([CH3:46])[C:12](=[CH:13][CH:14]=[C:15]4[C@@H:42]3[CH2:41][CH2:40][C@@:39]3([CH3:47])[C@H:16]4[CH2:17][CH2:18][C@@H:19]3[C@H:20]([CH3:38])[CH:21](S(C3C=CC=CC=3)(=O)=O)[CH2:22][C@@H:23]([OH:28])[C:24]([OH:27])([CH3:26])[CH3:25])[CH2:11]2)[CH2:4]1>CO.[Na].[Hg]>[O:3]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C@H:10]2[CH2:45][CH2:44][C@@:43]3([CH3:46])[C:12](=[CH:13][CH:14]=[C:15]4[C@@H:42]3[CH2:41][CH2:40][C@@:39]3([CH3:47])[C@H:16]4[CH2:17][CH2:18][C@@H:19]3[C@H:20]([CH3:38])[CH2:21][CH2:22][C@@H:23]([OH:28])[C:24]([OH:27])([CH3:26])[CH3:25])[CH2:11]2)[CH2:4]1

Komponenten

5

Edukt 2

HCID 141233DisodiumHCID 70546883(24R)-22xi-phenylsulfonyl-5,7-cholestadiene-3beta,24,25-triol 3-tetrahydropyranyl ether

Produkt 1

HCID 22821223(24R)-5,7-cholestadiene-3beta,24,25-triol 3-tetrahydropyranyl etherAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9837419Sodium amalgamKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A mixture of 1 g of anhydrous disodium hydrogenephosphate and 3.2 g of 5% sodium-amalgam was added to a solution of 160 mg of (24R)-22ξ-phenylsulfonyl-5,7-cholestadiene-3β,24,25-triol 3-tetrahydropyranyl ether in 5 ml of methanol in an argon stream under stirring, and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture 10 ml of methanol was added and the precipitate was filtered. The filtrate was evaporated under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydous sodium sulfate. The solvent was evaporated under reduced pressure to give 11.6 mg (93%) of (24R)-5,7-cholestadiene-3β,24,25-triol 3-tetrahydropyranyl ether.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. filtrationthe precipitate was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8dc725055a3c48629a0baad1201e99fe
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04344888

Verknüpfte Notizen

Wird geladen…