Hydrogen Peroxide → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutoxymethyl)androsta-5,7,16-triene

HRID 1792199ノート

反応式

HRID 1792199 の反応式
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[Si:15]([O:22][C@@H:23]1[C@@:40]2([CH3:41])[C:27](=[CH:28][CH:29]=[C:30]3[C@@H:39]2[CH2:38][CH2:37][C@@:35]2([CH3:36])[C@H:31]3[CH2:32][CH:33]=[C:34]2[CH2:42][O:43][CH2:44][CH:45]2[O:49][C:46]2([CH3:48])[CH3:47])[CH2:26][C@@H:25]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[CH2:24]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[OH-].[Na+].OO>O1CCCC1.C(OCC)(=O)C>[Si:15]([O:22][C@@H:23]1[C@@:40]2([CH3:41])[C:27](=[CH:28][CH:29]=[C:30]3[C@@H:39]2[CH2:38][CH2:37][C@@:35]2([CH3:36])[C@H:31]3[CH2:32][CH:33]=[C:34]2[CH2:42][O:43][CH2:44][CH2:45][C:46]([OH:49])([CH3:47])[CH3:48])[CH2:26][C@@H:25]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:52])[CH3:53])[CH2:24]1)([C:18]([CH3:21])([CH3:19])[CH3:20])([CH3:17])[CH3:16]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydride2 回HCID 86760153HCID 86760153、化合物

生成物 1

HCID 696305481alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(3-hydroxy-3-methylbutoxymethyl)androsta-5,7,16-triene収率 87%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

At room temperature, a solution of 1.0M L-SELECTRIDE in tetrahydrofuran (0.25 ml, 0.25 mmol) was added to a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(2,3-epoxy-3-methylbutoxymethyl)androsta-5,7,16-triene (48.3 mg, 0.0768 mmol) in tetrahydrofuran (2 ml) and stirred at the same temperature for 1 hour. To the solution, was further added a solution of 1.0M L-SELECTRIDE in tetrahydrofuran (0.2 ml, 0.2 mmol), followed by stirring at the same temperature for 1 hour. After cooling the reaction solution with ice, a 3N aqueous sodium hydroxide solution and then hydrogen peroxide solution were added. Immediately after the addition, the mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was purified by preparative thin layer chromatography (1 sheet (0.5 mm thickness), hexane:ethyl acetate=10:1, developed twice) to give the titled compound (42.0 mg, 87%) as a colorless oil.

後処理

  1. stirringby stirring at the same temperature for 1 hour
  2. temperatureAfter cooling the reaction solution with ice
  3. additionImmediately after the addition
  4. washwashed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure
  8. 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-c7fd4f7d8e38425ba62bc91da9c29ed4
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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