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4-Toluenesulfonyl chloride → (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| 反応物 | (25R)-16-oxo-26-hydroxycholesterol | HCID 13873472 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol | HCID 11729441 | 160.7% |
反応手順
To a solution of (25R)-26-hydroxy-16-oxocholesterol (9) (4.52 mmoles in pyridine (20 ml)), cooled in an ice bath, p-toluenesulfonyl chloride (3.44 g, 18.0 mmoles) is added mixture is stirred for 5 hours at room temperature. The reaction mixture is then poured into water and extracted with ether. The organic layer is washed with 2N HCl and water, dried over sodium sulfate, and evaporated under reduced pressure to yield 3.04 g (93%) of (25R)-16β, 26-dihydroxycholesterol 3β, 26-ditosylate (7) as an oil. The product is the same as the one in Example 8.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05274088 |
| 出典データセット | uspto-grants-1993_12 |
| ORD ID | ord-cee6e31dcfc14cb0a03a3e1ffc9785b2 |
| 出典メモ | uspto-grants-1993_12 |