3,4-dihydro-2H-pyran → (1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyl-dimethylsilyloxy-1-octenyl]-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

HRID 2226232ノート

反応式

HRID 2226232 の反応式
[Si:1]([O:8][CH:9]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])/[CH:10]=[CH:11]/[C@H:12]1[C@H:19]([OH:20])[CH2:18][C@H:17]2[C@@H:13]1[CH2:14][C:15](=[O:21])[O:16]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:27]1[CH:32]=[CH:31][CH2:30][CH2:29][CH2:28]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[Si:1]([O:8][CH:9]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])/[CH:10]=[CH:11]/[C@H:12]1[C@H:19]([O:20][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][O:27]2)[CH2:18][C@H:17]2[C@@H:13]1[CH2:14][C:15](=[O:21])[O:16]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 15224603(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one

生成物 1

HCID 15224604(1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyl-dimethylsilyloxy-1-octenyl]-7-tetrahydropyranyloxy-2-oxabicyclo[3.3.0]octan-3-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1S,5R,6R,7R)-6-[(E)-3(RS)-t-butyldimethylsilyloxy-1-octenyl]-7-hydroxy-2-oxabicyclo[3.3.0]octan-3-one (45) (4.69 g) in methylene chloride were added dihydropyran (5.17 g), and pyridinium p-toluenesufonate (0.77 g), and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was treated in the conventional manner and the obtained crude product was subjected to the silica gel column chromatography to give the title compound (46) as a mixture of the diastereomers.

後処理

  1. additionThe reaction mixture was treated in the conventional manner
  2. customthe obtained crude product

出典と根拠

ORDレコード
ord-7a06cbdd66b642488c75efd326f70285
出典データセット
uspto-grants-1994_09
特許番号
US05346921

反応ノート

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