Reacción #3130

ord-22a46d06c9484f61abcb3ba9fcd4507b

Ecuación de reacción

F.c1ccncc1
hydrogen fluoride-pyridine
CCCC[C@@H](C)C[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,17R)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate
→
CCCC[C@@H](C)C[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)OC)=C(OC(=O)c2ccccc2)C[C@H]1O
methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate
Rendimiento 28.0%

Reactantes

F.c1ccncc1
hydrogen fluoride-pyridine
CCCC[C@@H](C)C[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,17R)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-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 (0.7 ml) and methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (734 mg), the same procedure as in Example 2 was performed to obtain methyl(11R,12S,13E,15S,17R)-9-benzoyloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (141 mg, 28%)

Fuente

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