Reacción #3128

ord-a8c4e36b9c5748c2bdb42724db547b96

Ecuación de reacción

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)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-benzoyloxy-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)c2ccccc2)C[C@H]1O
methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienoate
Rendimiento 88.3%

Reactantes

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)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-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.3 ml) and methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate (239 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,13E,15S)-9-benzoyloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienoate (144 mg, 86%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05731452uspto-grants-1998_03