反応 #413363

ord-8edd289791b643e784bb05f2b78fda17

反応方程式

$CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1$

(5Z,13E)-(8R,9R,11R,12R,-15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy) 16,19-dimethyl-5,13,18-prostatrienoic acid

→

$CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@H](Cl)C[C@H]1O$

title compound

収率 14.6%

$CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@H](Cl)C[C@H]1O$

(5Z,13E)-(8R,9R,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic Acid

収率 14.6%

反応物

—

mixture

$CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)O)[C@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1$

(5Z,13E)-(8R,9R,11R,12R,-15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy) 16,19-dimethyl-5,13,18-prostatrienoic acid

試薬

なし

溶媒

acetic acid water tetrahydrofuran

反応条件

詳細条件

See reaction.notes.procedure_details.

後処理

1
その他The mixture was evaporated
2
その他under vacuum and the residue purified by column chromatography on silanized silica gel with ethanol/water (1:1)

実験手順

Under argon, 915 mg of (5Z,13E)-(8R,9R,11R,12R,-15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy) 16,19-dimethyl-5,13,18-prostatrienoic acid was stirred at room temperature for 17 hours with 19 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was evaporated thereafter under vacuum and the residue purified by column chromatography on silanized silica gel with ethanol/water (1:1), thus obtaining 94 mg of the title compound.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04444788uspto-grants-1984_04