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Water → 3beta-(2,3-Dihydroxypropoxy)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 1647635
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1647635
C[N+]1([O-])CC[O:5]CC1.[OH2:9].[CH2:10]([O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[CH2:27][CH2:26][C@@:24]2([CH3:25])[C@:20]3([OH:38])[CH2:21][CH2:22][C@@H:23]2[C:33]2[CH:37]=[CH:36][O:35][CH:34]=2)[CH2:15]1)[CH:11]=[CH2:12].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O.CC(C)=O>[OH:9][CH:11]([CH2:12][OH:5])[CH2:10][O:13][C@H:14]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:16]([CH2:17][CH2:18][C@@H:19]3[C@@H:28]2[CH2:27][CH2:26][C@@:24]2([CH3:25])[C@:20]3([OH:38])[CH2:21][CH2:22][C@@H:23]2[C:33]2[CH:37]=[CH:36][O:35][CH:34]=2)[CH2:15]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 228545783beta-Prop-2-enoxy-17beta(3-furyl)-5beta-androstan-14beta-ol

Produkt 1

HCID 700458923beta-(2,3-Dihydroxypropoxy)-17beta-(3-furyl)-5beta-androstan-14beta-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysator
HCID 180AcetoneLösungsmittel
HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a mixture of 0.70 g of N-Methylmorpholine-N-oxide, 6.5 ml of water, 13.7 ml of acetone and 1.64 ml of a 0.06 M ethereal osmium tetroxide solution, 2.0 g of 3β-prop-2-enoxy-17β(3-furyl)-5β-androstan-14β-ol, prepared as an intermediate in Ex.2, dissolved in 29 ml of tert-butanol were added at room temperature. The mixture was left on standing for 20 hrs, 50 ml of a saturated sodium hydrosulfite solution and 2.0 g of celite were added, the mixture was stirred for 2 hrs and then filtered. The organic solvent was distilled under reduced pressure, the aqueous phase was extracted with methylene chloride, the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 20/80 as eluant to give 1.8 g of 3β-(2,3-dihydroxypropoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white solid.

Aufarbeitung

  1. customprepared as an intermediate in Ex.2
  2. additionwere added at room temperature
  3. waitThe mixture was left
  4. filtrationfiltered
  5. distillationThe organic solvent was distilled under reduced pressure
  6. extractionthe aqueous phase was extracted with methylene chloride
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. customevaporated to dryness under reduced pressure
  9. customThe crude product was purified by flash-chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-0aa1e0a9a62946d5a3d8ec2c8d26f0f5
Quelldatensatz
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05432169

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