111136-40-4

Basic information

• Product Name: 6-Heptenoic acid, 3,5-dihydroxy-7-phenyl-, methyl ester, (3R,5S,6E)-
• CAS NO: 111136-40-4
• Molecular Formula: C14H18O4
• Molecular Weight: 250.295
• Mol File: 111136-40-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 6-Heptenoic acid, 3,5-dihydroxy-7-phenyl-, methyl ester, (3R,5S,6E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Heptenoic acid, 3,5-dihydroxy-7-phenyl-, methyl ester, (3R,5S,6E)-(111136-40-4)
• EPA Substance Registry System: 6-Heptenoic acid, 3,5-dihydroxy-7-phenyl-, methyl ester, (3R,5S,6E)-(111136-40-4)

Safety Data

• Hazardous Substances Data: 111136-40-4(Hazardous Substances Data)

Upstream product

• 141928-29-2 Methyl (+/-)-(6E)-5-Hydroxy-3-oxo-7-phenyl-6-heptenoate 
• 121712-61-6 methyl (E)-7-phenyl-3,5-dioxo-6-heptenoate 
• 55848-86-7 Methyl-(E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate 
• 14371-10-9 (E)-3-phenylpropenal 
• 74590-73-1 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 
• 116-11-0 2-Methoxypropene 
• 121786-82-1 (E)-methyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enoate 
• 104-55-2 3-phenyl-propenal 
• 105-45-3 acetoacetic acid methyl ester 
• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 
• 665003-66-7 (1S)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 

Downstream Products

• 70633-85-1 (4R,6S,1'E)-4-hydroxy-6-(2'-phenylvinyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 70670-14-3 (4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one 
• 109519-27-9 methyl (3S^*,5R^*)-3,5-isopropylidenedioxy-7-phenyl-6-heptenoate 
• 171598-87-1 (E)-(3R,5S)-Methyl 7-phenyl-syn-3,5-(isopropylidenedioxy)heptenoate 
• 913255-79-5 methyl 2-((2R,4S,5S,6R)-4,5-dihydroxy-6-phenyltetrahydro-2H-pyran-2-yl)acetate 

Relevant articles and documents

Short and efficient chemoenzymatic synthesis of goniothalamin

A high-yielding three-step synthesis of goniothalamin involving an enzymatic kinetic resolution in the presence of vinyl acrylate followed by ring-closing metathesis is discussed.

Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors

Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.

STUDIES ON THE DIASTEREOSELECTIVE REDUCTION OF β-HYDROXY KETONES TO 1,3-DIOLS WITH COMMON HYDRIDE REAGENTS

Some common reducing agents were employed in the diastereoselective reduction of several β-hydroxy ketones to their corresponding syn-1,3-diols.The use of NaBH4 with a Ti(IV) chelating species produced syn diols with a moderate to good selectivity significantly depending upon the reaction conditions chosen (solvent, temperature, nature of the titanium species).The use of LiAlH4 at low temperature, in the presence of LiI, showed a high selectivity for reduction to syn diols, thus demonstrating a possible chelating role of lithium.Some interesting preliminary results have been also obtained in the diastereoselective reduction of MEM-protected β-alkoxy ketones.