Reaktion #722203

ord-59277fc707da4ea7a4657b2525b17e1c

Reaktionsgleichung

CC[Si](CC)(CC)OC(C)(C)CCCS[C@@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(4-methyl-4-triethylsilyloxypentylthio)pregna-5,7,16-triene
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetra-n-butylammonium fluoride
→
C[C@H](SCCCC(C)(C)O)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 92.5%
C[C@H](SCCCC(C)(C)O)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)-(4-hydroxy-4-methylpentylthio)pregna-5,7,16-triene
Ausbeute 92.5%

Edukte

CC[Si](CC)(CC)OC(C)(C)CCCS[C@@H](C)C1=CC[C@H]2C3=CC=C4C[C@@H](O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@]4(C)[C@H]3CC[C@]12C
1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(4-methyl-4-triethylsilyloxypentylthio)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
    Sonstigethe residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane

Vorschrift

Under the same conditions as in Example 9, 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(4-methyl-4-triethylsilyloxypentylthio)pregna-5,7,16-triene (55.7 mg, 0.0825 mmol), tetrahydrofuran (2 ml) and IM tetra-n-butylammonium fluoride solution in tetrahydrofuran (2 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethanol=7:1, developed once) to give the title compound as a colorless oil (34.1 mg, 92%).

Quelle

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