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TBAF tetrahydrofuran → 20-(2-Ethyl-2-hydroxybutoxy)-1alpha,3beta-dihydroxy-20-methylpregna-5,7,16-triene

HRID 1792197
ノート
印刷プレビュー

反応式

HRID 1792197 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:21]([O:24][CH2:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:39][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:27]([C:26]([OH:29])([CH2:30][CH3:31])[CH2:25][O:24][C:21]([CH3:23])([C:20]1[C@:32]2([CH3:38])[C@H:17]([C:16]3[C@H:35]([CH2:34][CH2:33]2)[C@:36]2([CH3:37])[C:13]([CH2:12][C@@H:11]([OH:39])[CH2:10][C@@H:9]2[OH:8])=[CH:14][CH:15]=3)[CH2:18][CH:19]=1)[CH3:22])[CH3:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 11078149TBAF tetrahydrofuranHCID 696301181alpha,3beta-Bis(tert-butyldimethylsilyloxy)-20-(2-ethyl-2-hydroxybutoxy)-20-methylpregna-5,7,16-triene

生成物 1

HCID 6963022620-(2-Ethyl-2-hydroxybutoxy)-1alpha,3beta-dihydroxy-20-methylpregna-5,7,16-triene収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-(2-ethyl-2-hydroxybutoxy)-20-methylpregna-5,7,16-triene (32.0 mg, 0.0475 mmol), a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (0.3 ml, 0.3 mmol) and tetrahydrofuran (0.5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (reflux under heating for 16 hours), worked up and the thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), hexane:ethyl acetate:ethanol=10:5:1, developed twice) to give the titled compound (19.8 mg, 94%) as a colorless oil.

後処理

  1. temperatureof Example 5(2) (reflux under heating for 16 hours)
  2. customthe thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), hexane

出典と根拠

ORDレコード
ord-119241f1e30f4606852a9293fbdb4883
出典データセット
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07074777B2

反応ノート

読み込み中…

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