146579-02-4

Basic information

• Product Name: methyl (3S,5R,6E)-8-di(4-fluorophenyl)methylidene-3,5-isopropylidenedioxy-9-methyl-6-decenoate
• CAS NO: 146579-02-4
• Molecular Weight: 470.556
• Mol File: 146579-02-4.mol

Chemical Properties

• CAS DataBase Reference: methyl (3S,5R,6E)-8-di(4-fluorophenyl)methylidene-3,5-isopropylidenedioxy-9-methyl-6-decenoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3S,5R,6E)-8-di(4-fluorophenyl)methylidene-3,5-isopropylidenedioxy-9-methyl-6-decenoate(146579-02-4)
• EPA Substance Registry System: methyl (3S,5R,6E)-8-di(4-fluorophenyl)methylidene-3,5-isopropylidenedioxy-9-methyl-6-decenoate(146579-02-4)

Safety Data

• Hazardous Substances Data: 146579-02-4(Hazardous Substances Data)

Upstream product

• 109519-24-6 methyl (3S,5R)-3,5-isopropylidenedioxy-6-oxohexanoate 
• 146579-00-2 2-di(4-fluorophenyl)methylidene-3-methylbutyl(diphenyl)phosphine oxide 
• 109583-02-0 methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate 
• 345-92-6 4,4'-Difluorobenzophenone 
• 118559-08-3 ethyl 3,3-bis(4-fluorophenyl)-2-(1-methylethyl)propenoate 
• 118559-09-4 2-di(4-fluorophenyl)methylene-3-methyl-1-butanol 
• 108-64-5 Ethyl isovalerate 

Downstream Products

• 135972-32-6 (E,3S,5R)-8-bis(4-fluorophenyl)methylidene-3,5-dihydroxy-9-methyl-6-decenoic acid 1,5-lactone 

Relevant articles and documents

Synthesis of artificial HMG-CoA reductase inhibitors based on the olefination strategy

Synthetic methods were studied for optically active 6-oxo-3,5-isopropylidenedioxyhexanoate esters (4), which could be used as a key precursor of various kinds of artificial analogs of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors. An enantiomer (+)-4 was prepared by asymmetric reduction of β,δ-diketo esters derived from the Taber's alcohol or L-tartrate followed by a series of chemical transformations, and the desired enantiomer (-)-4 was prepared by the same asymmetric reduction starting from D-tartrate. The key intermediate (-)-4 was finally converted into a highly potent HMG-CoA reductase inhibitor, NK-104.

A novel enantioselective synthesis of HMG Co-A reductase inhibitor NK-104 and a related compound

Optically active methyl 6-oxo-3,5-syn-isopropylidenedioxyhexanoate (5) was prepared by enantioselective syn-reduction of β,δ-diketo ester 2, followed by hydrolysis, protection of the diol moiety and ozonolysis, and was converted into a highly potent HMG Co-A reductase inhibitor NK-104 and an analogue.