- Synthesis of Simvastatin
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(CAS NO.: ), with its systematic name of Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, could be produced through many synthetic methods.
Following is one of the synthesis routes:
The deacylation of lovastatin (I) with aqueous LiOH affords the free diol (II), which is partially protected with tert-butyldimethylsilyl chloride as usual, producing the monosilylated derivative (III). The acylation of (III) with 2,2-dimethylbutyryl chloride (IV) in the presence of 4-pyrrolidino pyridine (py-py) in pyridine affords the silylated ester (V), which is finally deprotected with tetrabutylammonium fluoride and acetic acid in THF.
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