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Benzoic anhydride → methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Benzoic anhydride | HCID 7167 | — |
| 反応物 | (3S)-1-Iodo-3-(tert-butyldimethylsilyloxy)-1-octene | HCID 11111369 | — |
| 反応物 | (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonylpentylthio)-2-cyclopenten-1-one | HCID 131720587 | — |
| 反応物 | HCID 178418306 | HCID 178418306 | — |
| 反応物 | C6H9Cu | HCID 178418419 | — |
| 溶媒 | Hexamethylphosphorous triamide | HCID 15355 | — |
| 生成物 | methyl(11R,12S,13E,15S)-9-benzoyloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienoate | HCID 22883804 | 55.4% |
反応手順
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%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05731452 |
| 出典データセット | uspto-grants-1998_03 |
| ORD ID | ord-76d32aafd0e142d0832c397f95f52a05 |
| 出典メモ | uspto-grants-1998_03 |