Reaktion #722214

ord-94e4ddbbf52c47c9913d944adf9aeccb

Reaktionsgleichung

CCC(CC)[C@@H](O)CS[C@@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-{3-ethyl-2(R)-hydroxypentylthio}pregna-5,7,16-triene
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetra-n-butylammonium fluoride
→
CCC(CC)[C@@H](O)CS[C@@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C
title compound
Ausbeute 103.2%
CCC(CC)[C@@H](O)CS[C@@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C
1α,3β-dihydroxy-20(S)-{3-ethyl-2(R)-hydroxypentylthio}pregna-5,7,16-triene
Ausbeute 103.2%

Edukte

CCC(CC)[C@@H](O)CS[C@@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-{3-ethyl-2(R)-hydroxypentylthio}pregna-5,7,16-triene
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetra-n-butylammonium fluoride

Reagenzien

Keine

Lösungsmittel

C1CCOC1
tetrahydrofuran
C1CCOC1
tetrahydrofuran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperatur(heating under reflux for 5 hours)
  2. 2
    Sonstigethe residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane

Vorschrift

By the same procedure as in Example 9, 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-{3-ethyl-2(R)-hydroxypentylthio}pregna-5,7,16-triene (54.9 mg, 0.0797 mmol), tetrahydrofuran (3 ml) and 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (2 ml) were reacted (heating under reflux for 5 hours) and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethanol=9:1, developed once) to give the title compound as a colorless oil (37.9 mg, 100%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06184398B2uspto-grants-2001_02