Reaktion #3131

ord-d5c0f98feabe41e293e98aa397fcf97a

Reaktionsgleichung

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate
→
CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O
methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-dienoate
Ausbeute 51.0%

Edukte

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)[C@H](Cc2ccccc2)NC(=O)OCc2ccccc2)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (140 mg), methyl(11R,12S,13E,15S)-9-(N-benzyloxycarbonylphenylalanyloxy)-11,15-dihydroxy-7-thiaprosta-8,13-dienoate (53 mg, 51%) was obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731452uspto-grants-1998_03