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

HRID 1792231노트

반응식

HRID 1792231 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e72c3fca4eec478aaf6d88c4e7c5a54d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074777B2

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