TBAF tetrahydrofuran → 1alpha,3beta-Dihydroxy-17beta-(4-ethyl-4-hydroxyhexyloxymethyl)androsta-5,7-diene

HRID 1792231ノート

反応式

HRID 1792231 の反応式
[Si]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][O:29][CH2:30][CH2:31][CH2:32][C:33]([CH2:44][CH3:45])([O:36][Si](CC)(CC)CC)[CH2:34][CH3:35])[CH2:12][C@@H:11]([O:46][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[OH:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][O:29][CH2:30][CH2:31][CH2:32][C:33]([CH2:34][CH3:35])([OH:36])[CH2:44][CH3:45])[CH2:12][C@@H:11]([OH:46])[CH2:10]1

参加物

4

反応物 2

HCID 11078149TBAF tetrahydrofuranHCID 696305921alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17beta-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene

生成物 1

HCID 696301481alpha,3beta-Dihydroxy-17beta-(4-ethyl-4-hydroxyhexyloxymethyl)androsta-5,7-diene収率 98.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-{4-ethyl-4-(triethylsilyloxy)hexyloxymethyl}androsta-5,7-diene (180 mg), was added a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (6 ml), followed by reflux under heating for 5 hours. After adding ethyl acetate, the mixture was washed with saturated brine, a saturated aqueous sodium bicarbonate solution and then saturated brine. The organic layer was dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove the solvent and the resulting residue was purified by column chromatography (ethyl acetate) to give the titled compound (0.10 g).

後処理

  1. temperatureby reflux
  2. temperatureunder heating for 5 hours
  3. washthe mixture was washed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customthe resulting residue was purified by column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-e72c3fca4eec478aaf6d88c4e7c5a54d
出典データセット
uspto-grants-2006_07
特許番号
US07074777B2

反応ノート

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