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

HRID 1647645
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HRID 1647645 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e7f8b879f16149c8b32ceb1c1050ed75
출처 데이터셋
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05432169

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