Reaktion #3127
ord-76d32aafd0e142d0832c397f95f52a05
Reaktionsgleichung
(4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one
(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene
tert-butyllithium
benzoic anhydride
1-hexynylcopper
→
methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate
Ausbeute 55.4%
Edukte
Reagenzien
Keine
Lösungsmittel
Reaktionsbedingungen
Detaillierte Bedingungen
See reaction.notes.procedure_details.
Vorschrift
Using as the materials and reagents (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (442 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 1-hexynylcopper (174 mg), hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonyl-pentylthio)-2-cyclopenten-1-one (373 mg, 1.0 mmol), and benzoic anhydride (661 mg), the same procedure was performed as in Example 1 to obtain methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg, 33%).