81189-93-7

Basic information

• Product Name: (2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate
• Synonyms: (2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate
• CAS NO: 81189-93-7
• Molecular Weight: 508.655
• Mol File: 81189-93-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate(81189-93-7)
• EPA Substance Registry System: (2R,4R)-2-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-6-oxo-2H-pyran-4-yl benzoate(81189-93-7)

Safety Data

• Hazardous Substances Data: 81189-93-7(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 75330-75-5 lovastatin 

Downstream Products

• 123049-81-0 simvastatin 
• 479482-39-8 (2R,4R)-2,2-(ethylenedioxy)-6-[2-((1S,2S,6R,8S,8aR)-1,2,3,7,8,8a-hexahydro-2,6-dimethyl-8-{[(S)-2-methylbutanoyl]oxy}naphthalen-1-yl)ethyl]-3,4,5,6-tetrahydro-2H-pyran-4-yl benzoate 

Relevant articles and documents

A new method for the synthesis of antihypercholesterolemic agent simvastatin

A new synthetic method for the preparation of the cholesterol-lowering drug simvastatin from the naturally occurring lovastatin is reported. The synthesis employs first the protection of the OH group of lovastatin (1) and then the protection of the lactone C=O group to prevent enolization via conversion to the orthoesters 4a and 4b. Alkylation of the 2-methylbutyrate side chain is then successfully achieved. Removal of the protecting groups affords antihypercholesterolemic agent simvastatin (2).