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

HRID 1792197
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HRID 1792197 반응식
[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]
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-119241f1e30f4606852a9293fbdb4883
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07074777B2

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