Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether → HCID 54474221, compound

HRID 2396238Notes

Reaction equation

HRID 2396238 reaction equation
[CH2:1]([O:3][C:4]([CH2:10][CH3:11])([CH2:8][CH3:9])[C:5]([OH:7])=[O:6])[CH3:2].[Si:12]([O:19][C@H:20]1[CH2:29][C@H:28](O)[C@H:27]2[C:22]([CH:23]=[CH:24][C@H:25]([CH3:48])[C@@H:26]2[CH2:31][CH2:32][C@H:33]2[O:38][C:37](=[O:39])[CH2:36][C@H:35]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:34]2)=[CH:21]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>>[Si:12]([O:19][C@H:20]1[CH2:29][C@H:28]([O:6][C:5](=[O:7])[C:4]([O:3][CH2:1][CH3:2])([CH2:8][CH3:9])[CH2:10][CH3:11])[C@H:27]2[C:22]([CH:23]=[CH:24][C@H:25]([CH3:48])[C@@H:26]2[CH2:31][CH2:32][C@H:33]2[O:38][C:37](=[O:39])[CH2:36][C@H:35]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:42])[CH3:43])[CH2:34]2)=[CH:21]1)([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) EtherHCID 18988574HCID 18988574, compound

Product 1

HCID 54474221HCID 54474221, compoundYield 21.5%

Procedure

A procedure similar to that described in Example 10, above, was followed, but using 875 mg of 2-ethoxy-2-ethylbutyric 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 271 mg of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-da2dbb16553743468aabaab005fc8210
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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