109583-02-0

Basic information

• Product Name: methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate
• Synonyms: methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate
• CAS NO: 109583-02-0
• Molecular Weight: 290.359
• Mol File: 109583-02-0.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate(109583-02-0)
• EPA Substance Registry System: methyl (3S,5R,6E)-7-phenyl-3,5-isopropylidenedioxy-6-heptenoate(109583-02-0)

Safety Data

• Hazardous Substances Data: 109583-02-0(Hazardous Substances Data)

Upstream product

• 109519-22-4 (3S,5R)-6,6-Bis-ethylsulfanyl-3,5-dihydroxy-hexanoic acid methyl ester 
• 96852-88-9 3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-hex-5-enofuranoside 
• 109519-23-5 [(4S,6R)-6-(Bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester 
• 109536-54-1 methyl 1,2-O-isopropylidene-3,5-dideoxy-α-D-glucofuranose 
• 58475-20-0 3,5-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranose 
• 116-11-0 2-Methoxypropene 
• 121786-82-1 (E)-methyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enoate 
• 142033-86-1 methyl (3S,5R,6E)-7-phenyl-3,5-dihydroxy-6-heptenoate 
• 77-76-9 2,2-dimethoxy-propane 
• 103338-09-6 methyl (E,3S^*,5R^*)-3,5-dihydroxy-7-phenyl-6-heptenoate 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 109519-24-6 methyl (3S,5R)-3,5-isopropylidenedioxy-6-oxohexanoate 

Downstream Products

• 118918-05-1 trans-(4R,6S)-6-[4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl]-tetrahydro-4-hydroxy-2H-pyran-2-one 
• 129785-03-1 (E)-(3R,5S)-9,9-Bis-(4-fluoro-phenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-nona-6,8-dienoic acid 
• 118845-88-8 [(4R,6S)-2,2-Dimethyl-6-((E)-styryl)-[1,3]dioxan-4-yl]-acetic acid 
• 130320-56-8 BMY-21950 
• 118845-89-9 cis-(4R,6S)-6-<4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl>-2,2-dimethyl-1,3-dioxane-4-acetic acid 
• 22639-28-7 (R)-goniothalamin 
• 135972-32-6 (E,3S,5R)-8-bis(4-fluorophenyl)methylidene-3,5-dihydroxy-9-methyl-6-decenoic acid 1,5-lactone 
• 146579-01-3 ((4S,6R)-6-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid methyl ester 
• 146579-02-4 methyl (3S,5R,6E)-8-di(4-fluorophenyl)methylidene-3,5-isopropylidenedioxy-9-methyl-6-decenoate 
• 70670-14-3 (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one 
• 118845-88-8 cis-2,2-dimethyl-6-(2-phenylethenyl)-1,3-dioxane-4-acetic acid 

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.

Antihypercholesterolemic tetrazole compounds

Compounds of the formula STR1 wherein R1 and R4 each are independently hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, or trifluoromethyl; R2, R3, R5 and R6 each are independently hydrogen, halogen C1-4 alkyl or C1-4 alkoxy; tet is STR2 n is an integer of from 0 to 2, inclusive; A is STR3 R7 is hydrogen, C1-4 alkyl, C1-4 alkoxy(lower) alkyl or (2-methoxyethoxy)methyl; X is --OH or =O; and R8 is hydrogen, a hydrolyzable ester group or a cation to form a non-toxic pharmaceutically acceptable salt, are novel antihypercholesterolemic agents which inhibit cholesterol biosynthesis. Intermediates and processes for their preparation are disclosed.