Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether → (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(4-t-butylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one
Reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH:10]([CH2:14][CH3:15])[C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:18]([C@H:26]1[CH2:35][C@H:34](O)[C@H:33]2[C:28]([CH:29]=[CH:30][C@H:31]([CH3:54])[C@@H:32]2[CH2:37][CH2:38][C@H:39]2[O:44][C:43](=[O:45])[CH2:42][C@H:41]([O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[CH2:40]2)=[CH:27]1)[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>>[Si:19]([O:18][C@H:26]1[CH2:35][C@H:34]([O:12][C:11](=[O:13])[CH:10]([O:9][C:8]2[CH:16]=[CH:17][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=2)[CH2:14][CH3:15])[C@H:33]2[C:28]([CH:29]=[CH:30][C@H:31]([CH3:54])[C@@H:32]2[CH2:37][CH2:38][C@H:39]2[O:44][C:43](=[O:45])[CH2:42][C@H:41]([O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:48])[CH3:49])[CH2:40]2)=[CH:27]1)([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20]Participants
3
Reactant 2
Product 1
Procedure
A procedure similar to that described in Example 1, above, was followed, but using 803 mg of (2RS)-2-(4-t-butylphenoxy)butyric acid and 1.0 g of (4R,6R)-6-{(1S,2S,6S,8S,8aR)-2-[1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsiloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above], to give 1.41g of the title compound as a colorless foam.
Sources & evidence
- ORD record
- ord-36a25a63608247dc9a669635d7a43005
- Source dataset
- uspto-grants-1996_02
- Patent number
- US05491167
Reaction notes
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