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

HRID 434511

反応式

HRID 434511 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b31b37c0d51d44f59c5415282e5f735b
出典データセット
uspto-grants-1983_08
特許番号
US04397847

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