Disodium → (24R)-5,7-cholestadiene-3beta,24,25-triol 3-tetrahydropyranyl ether

HRID 67048

反応式

HRID 67048 の反応式
[Na][Na].[O:3]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C@H:10]2[CH2:45][CH2:44][C@@:43]3([CH3:46])[C:12](=[CH:13][CH:14]=[C:15]4[C@@H:42]3[CH2:41][CH2:40][C@@:39]3([CH3:47])[C@H:16]4[CH2:17][CH2:18][C@@H:19]3[C@H:20]([CH3:38])[CH:21](S(C3C=CC=CC=3)(=O)=O)[CH2:22][C@@H:23]([OH:28])[C:24]([OH:27])([CH3:26])[CH3:25])[CH2:11]2)[CH2:4]1>CO.[Na].[Hg]>[O:3]1[CH2:8][CH2:7][CH2:6][CH:5]([O:9][C@H:10]2[CH2:45][CH2:44][C@@:43]3([CH3:46])[C:12](=[CH:13][CH:14]=[C:15]4[C@@H:42]3[CH2:41][CH2:40][C@@:39]3([CH3:47])[C@H:16]4[CH2:17][CH2:18][C@@H:19]3[C@H:20]([CH3:38])[CH2:21][CH2:22][C@@H:23]([OH:28])[C:24]([OH:27])([CH3:26])[CH3:25])[CH2:11]2)[CH2:4]1

参加物

5

反応物 2

HCID 141233DisodiumHCID 70546883(24R)-22xi-phenylsulfonyl-5,7-cholestadiene-3beta,24,25-triol 3-tetrahydropyranyl ether

生成物 1

HCID 22821223(24R)-5,7-cholestadiene-3beta,24,25-triol 3-tetrahydropyranyl ether収率 93%

試薬・触媒・溶媒 2

HCID 9837419Sodium amalgam触媒HCID 887Methanol溶媒2 回

実験手順

A mixture of 1 g of anhydrous disodium hydrogenephosphate and 3.2 g of 5% sodium-amalgam was added to a solution of 160 mg of (24R)-22ξ-phenylsulfonyl-5,7-cholestadiene-3β,24,25-triol 3-tetrahydropyranyl ether in 5 ml of methanol in an argon stream under stirring, and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture 10 ml of methanol was added and the precipitate was filtered. The filtrate was evaporated under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydous sodium sulfate. The solvent was evaporated under reduced pressure to give 11.6 mg (93%) of (24R)-5,7-cholestadiene-3β,24,25-triol 3-tetrahydropyranyl ether.

後処理

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. filtrationthe precipitate was filtered
  3. customThe filtrate was evaporated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-8dc725055a3c48629a0baad1201e99fe
出典データセット
uspto-grants-1982_08
特許番号
US04344888

関連ノート

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