Tetrabutylammonium Fluoride → 1alpha,3beta-Dihydroxy-20(S)-(3-ethyl-3hydroxypentylthio)pregna-5,7,16-triene

HRID 2304198ノート

反応式

HRID 2304198 の反応式
[Si]([O:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])[CH3:22])[CH2:12][C@@H:11]([OH:39])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C@@H:9]1[C@@:36]2([CH3:37])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:35]2[CH2:34][CH2:33][C@@:32]2([CH3:38])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])[CH3:22])[CH2:12][C@@H:11]([OH:39])[CH2:10]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 120195171alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-(3-ethyl-3-hydroxypentylthio)pregna-5,7,16-triene

生成物 1

HCID 120195231alpha,3beta-Dihydroxy-20(S)-(3-ethyl-3hydroxypentylthio)pregna-5,7,16-triene収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under the same conditions as in Example 9, the crude 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-(3-ethyl-3-hydroxypentylthio)pregna-5,7,16-triene obtained in Example 7, tetrahydrofuran (2 ml) and 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (2 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane:ethanol=7:1, developed once) to give the title compound as a colorless oil (42.0 mg, 64%, 2 steps).

後処理

  1. customthe residue was purified by preparative thin layer chromatography (0.5 mm×2, dichloromethane

出典と根拠

ORDレコード
ord-de7996782e1a4e959cc905e919b1b1d9
出典データセット
uspto-grants-2002_08
特許番号
US06433200B1

反応ノート

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