Tetrahydrofuran → [1alpha,3beta]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one

HRID 745641

반응식

HRID 745641 반응식
[OH:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])[CH2:5][C@@H:4]([OH:22])[CH2:3]1.[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[O:28]1[CH:33]=[CH:32][CH2:31][CH2:30][CH2:29]1.O.[C:35]1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:35]1[O:1][C@@H:2]1[C@@:19]2([CH3:20])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:21])[CH2:5][C@@H:4]([O:22][CH:33]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[CH2:3]1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 1679551-HydroxydehydroepiandrosteroneHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 13189253[1alpha,3beta]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 0.91 g (0.0030 mol) of 1α,3β-dihydroxyandrost-5-en-17-one [R. M. Dodson, A. H. Goldkamp and R. D. Muir, J.Amer.Chem.Soc., 82, 4026 (1960)], 15 mL of tetrahydrofuran, 1.26 g (0.015 mol) of 3,4-dihydro-2H-pyran and 0.028 g of p-toluenesulfonic acid monohydrate was stirred at 25° for 18 hr. The mixture was diluted with methylene chloride. This solution was then washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to yield oily [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]androst-5-en-17-one, [α]D20 +34.3° (c 1, CHCl3).

후처리

  1. washThis solution was then washed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-57c4f52724f54c2388446475f8e525ab
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599330

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