Water → (1S,2RS,5S,6S,7R)-2-(2-tetrahydropyranyloxy)-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyl-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

HRID 1974775ノート

反応式

HRID 1974775 の反応式
[OH:1][CH:2]1[C:9](=[CH2:10])[CH2:8][C@H:7]2[C@@H:3]1[CH2:4][C@@H:5]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C@H:6]2/[CH:11]=[CH:12]/[C@@H:13]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[O:35]1[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36]1.O>C(Cl)Cl.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>[O:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH:40]1[O:1][CH:2]1[C:9](=[CH2:10])[CH2:8][C@H:7]2[C@@H:3]1[CH2:4][C@@:5]([C:3]([CH3:7])([CH3:4])[CH3:2])([O:27][Si:28]([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:29])[CH3:30])[C@H:6]2/[CH:11]=[CH:12]/[C@@H:13]([O:19][Si:20]([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:21])[CH3:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

6

反応物 3

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 13955240(1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane

生成物 1

HCID 22850338(1S,2RS,5S,6S,7R)-2-(2-tetrahydropyranyloxy)-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyl-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane収率 176%

試薬・触媒・溶媒 2

HCID 21909214Pyridium p-toluenesulfonate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

(1S,2RS,5S,6S,7R)-2-hydroxy-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (127 mg, 0.25 mmole) obained in Example 3 was dissolved in 2 ml of methylene chloride. Dihydropyrane (42 mg, 0.50 mmole) and pyridium p-toluenesulfonate (5 mg) were added to the solution, and the mixture was stirred at room temperature for 8 hours. Water and methylene chloride were added to the reaction mixture to perform extraction. The resulting organic layer was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The resulting crude product was subjected to column chromatography (silica gel 15 g, hexane/ethyl acetate=30/1) to give (1S,2RS,5S,6S,7R)-2-(2-tetrahydropyranyloxy)-3-methylene-6-[(E,3S)-3-t-butyldimethylsilyloxy-1-octenyl]-7-t-butyl-7-t-butyldimethylsilyloxybicyclo[3.3.0]octane (130 mg, 0.22 mmole, 88%).

後処理

  1. extractionextraction
  2. washThe resulting organic layer was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-d3f358db81d94d6ebdf9cee7a1fbc034
出典データセット
uspto-grants-1994_02
特許番号
US05283349

反応ノート

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