Dehydroepiandrosterone → Dehydroepiandrosterone

HRID 48957

Reaktionsgleichung

Reaktionsgleichung von HRID 48957
O1C(O)C[C@@H](C(C)C)C[CH:2]1[C@H]([C@@H]1[C@]2(C)[C@@H]([C@H]3[C@H](CC2)[C@]2(C)C(CC(O)CC2)CC3)C(=O)C1)C.[CH3:34][C@@:35]12[C:43](=[O:44])[CH2:42][CH2:41][C@H:40]1[C@@H:39]1[CH2:45][CH:46]=[C:47]3[CH2:52][C@@H:51]([OH:53])[CH2:50][CH2:49][C@:48]3([CH3:54])[C@H:38]1[CH2:37][CH2:36]2>>[C:2].[C:34].[CH3:34][C@@:35]12[C:43](=[O:44])[CH2:42][CH2:41][C@H:40]1[C@@H:39]1[CH2:45][CH:46]=[C:47]3[CH2:52][C@@H:51]([OH:53])[CH2:50][CH2:49][C@:48]3([CH3:54])[C@H:38]1[CH2:37][CH2:36]2

Komponenten

4

Edukt 2

HCID 5881DehydroepiandrosteroneHCID 6962581522,29-EPOXY-3,29-DIHYDROXY-14beta-STIGMASTAN-15-ONE

Produkt 2

HCID 5881DehydroepiandrosteroneHCID 178420941HCID 178420941, Verbindung

Versuchsvorschrift

The synthesis of 22,29-epoxy-3,29-dihydroxy-14β-stigmastan-15-one (260) can be accomplished in ten steps from dehydroisoandrosterone (247). Catalytic hydrogenation of the Δ5 carbon-carbon double bond in compound 247 yields compound 250, which contains a trans-fused A/B ring-system. Compound 247 is dissolved in EtOAc and 10% Pd/C is added. The mixture is stirred under H2 at room temperature overnight. Filtration through celite and concentration yields compound 250, which can be used directly in the next reaction.

Quellen und Nachweise

ORD-Eintrag
ord-d863766c08014899a9c4dffcca1796e9
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706701B1

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