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-(2-t-butylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

HRID 2396222Notes

Reaction equation

HRID 2396222 reaction equation
[C:1]([C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=1[O:7][CH:8]([CH2:12][CH3:13])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[Si:18]([O:25][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)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>>[Si:18]([O:25][C@H:26]1[CH2:35][C@H:34]([O:10][C:9](=[O:11])[CH:8]([O:7][C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:12][CH3:13])[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:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19]

Participants

3

Reactant 2

HCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) EtherHCID 18988619(2RS)-2-(2-t-butylphenoxy)butyric acid

Product 1

HCID 67675824(4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-(2-t-butylphenoxy)butyryloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-oneYield 104.6%

Procedure

A procedure similar to that described in Example 1, above, was followed, but using 0.86 g of (2RS)-2-(2-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-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above], to give 1.46 g of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-a3605602b3964bbc85a372be4b4e6c40
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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