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Triphenylphosphine → 3beta-Acetylthio-14beta,15beta-epoxy-17beta-(3-furyl)-5beta-androstane

HRID 1647645
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1647645
N(C(OC(C)C)=O)=NC([O:5][CH:6]([CH3:8])C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:34]1[C@@H:36]2[CH2:37][C@H:38]([C:55]3[CH:59]=[CH:58][O:57][CH:56]=3)[C@:39]3([CH2:41][CH2:42][C@H:43]4[C@H:52]([C@@:35]123)[CH2:51][CH2:50][C@H:49]1[C@:44]4([CH3:54])[CH2:45][CH2:46][C@@H:47](O)[CH2:48]1)[CH3:40].[S:60]1C=CC=C1CC(O)=O>O1CCCC1>[C:6]([S:60][C@H:47]1[CH2:46][CH2:45][C@@:44]2([CH3:54])[C@H:49]([CH2:50][CH2:51][C@@H:52]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@:35]43[O:34][C@@H:36]4[CH2:37][C@@H:38]2[C:55]2[CH:59]=[CH:58][O:57][CH:56]=2)[CH2:48]1)(=[O:5])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 8674878914beta,15beta-Epoxy-17beta-(3-furyl)-5beta-androstan-3alpha-ol

Produkt 1

HCID 867487913beta-Acetylthio-14beta,15beta-epoxy-17beta-(3-furyl)-5beta-androstane

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Diisopropyl azodicarboxylate (3.5 ml) was added to a solution of 4.5 g of triphenylphosphine in 85 ml of tetrahydrofuran at 0° C. and the mixture was stirred for 30'. To this mixture a solution of 2.0 g of 14β,15β-epoxy-17β-(3-furyl)-5β-androstan-3α-ol and 2.05 ml of thiolacetic acid in 90 ml of tetrahydrofuran was added dropwise and the resulting mixture was stirred for an hr at room temperature. The solvent was evaporated to dryness under reduced pressure and the crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 95/5 as eluant to give 1.7 g of the title compound (VI-b) as a white solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for an hr at room temperature
  2. customThe solvent was evaporated to dryness under reduced pressure
  3. customthe crude product was purified by flash-chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-e7f8b879f16149c8b32ceb1c1050ed75
Quelldatensatz
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05432169

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