Hydrogen Peroxide → (3 R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene

HRID 258449ノート

反応式

HRID 258449 の反応式
[N+](C1C=CC=CC=1[Se]C#N)([O-])=O.[CH2:13]([O:20][C@@H:21]([C@@H:28]([CH2:45][CH2:46]O)[CH:29]=[CH:30][C@@H:31]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:22][CH:23]([O:26][CH3:27])[O:24][CH3:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(P(CCCC)CCCC)CCC.OO>O1CCCC1>[CH2:13]([O:20][C@@H:21]([C@@H:28]([CH:45]=[CH2:46])[CH:29]=[CH:30][C@@H:31]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:22][CH:23]([O:26][CH3:27])[O:24][CH3:25])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 13831TributylphosphineHCID 1039312-Nitrophenyl selenocyanateHCID 67862831(3R,4S,7S) 3,7-dibenzyloxy-4-(2'-hydroxyethyl)-1,1-dimethoxydodeca-5-ene

生成物 1

HCID 67862608(3 R,4S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 997 mg (3.67 mM) of o-nitrophenylselenium cyanide in 12 ml of anhydrous tetrahydrofuran was dropwise added 886 mg (1.83 mM) of (3R,4S,7S) 3,7-dibenzyloxy-4-(2'-hydroxyethyl)-1,1-dimethoxydodeca-5-ene [7] described above. The mixture was stirred for several minutes and 0.91 ml (3.67 mM) of tri-n-butylphosphine was dropwise added to the mixture. The reaction solution was stirred for ten minutes then cooled to 0° C. and 35% hydrogen peroxide aqueous solution was dropwise added thereto at the same temperature while stirring. After stirring for 3 hours, the aqueous phase was extracted with a solvent mixture of diethyl ether:hexane=7:3. The extracts were combined and washed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The precipitated crystals were taken from the residue by filtration to give 776 mg (1.67 mM) of (3R,4 S,7S) 3,7-dibenzyloxy-4-vinyl-1,1-dimethoxydodeca-5-ene [8]. Yield, 91%.

後処理

  1. stirringThe reaction solution was stirred for ten minutes
  2. stirringat the same temperature while stirring
  3. stirringAfter stirring for 3 hours
  4. extractionthe aqueous phase was extracted with a solvent mixture of diethyl ether
  5. washwashed sequentially with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. filtrationThe precipitated crystals were taken from the residue by filtration

出典と根拠

ORDレコード
ord-486a94eadf0f478f89dbf7df18e75c3e
出典データセット
uspto-grants-1993_11
特許番号
US05266703

反応ノート

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