(3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid

Base Information

• Chemical Name: (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid
• CAS No.: 254452-86-3
• Molecular Formula: C₂₅H₂₄FNO₄
• Molecular Weight: 421.468
• Hs Code.: 29334900
• Mol file: 254452-86-3.mol

Synonyms:(3S,5R,E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoic acid;;

Chemical Property of (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid

Chemical Property:

• Boiling Point: 692.0±55.0 °C(Predicted)
• PKA: 4.24±0.10(Predicted)
• PSA: 90.65000
• Density: 1.352±0.06 g/cm3(Predicted)
• LogP: 4.51810
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

(3S,5R,E)-7-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxyhept-6-enoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid

There total 7 articles about (3S,5R,6E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3S,5R,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoate (141750-58-5) → (4S)-3-exo-(1-naphthyl)-4,7,7-trimethylbicyclo[2.2.1]heptan-2-exo-ol (86835-18-9) + (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid (254452-86-3,147511-69-1,688735-41-3,769908-13-6,121659-03-8)

Guidance literature:

With sodium hydroxide; In methanol; for 12h; Ambient temperature;

DOI:10.1246/bcsj.68.350

Reference yield:

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5) → (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid (254452-86-3,147511-69-1,688735-41-3,769908-13-6,121659-03-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMSO; P₂O₅; Et₃N

2.1: NaOH; (n-octyl)3MeNCl / toluene; H₂O

3.1: DIBAH

4.1: NaH; n-BuLi

5.1: NaBH₄; Et₂BOMe / -78 °C

6.1: aq. NaOH

6.2: (-)-α-methylbenzylamine

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; phosphorus pentoxide; Aliquat 336; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In water; toluene; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Condensation / 5.1: Reduction / 6.1: Hydrolysis / 6.2: resolution;

DOI:10.1016/S0960-894X(99)00519-3

Reference yield:

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline (121660-37-5) → (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid (254452-86-3,147511-69-1,688735-41-3,769908-13-6,121659-03-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOH; (n-octyl)3MeNCl / toluene; H₂O

2.1: DIBAH

3.1: NaH; n-BuLi

4.1: NaBH₄; Et₂BOMe / -78 °C

5.1: aq. NaOH

5.2: (-)-α-methylbenzylamine

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; diethyl methoxy borane; Aliquat 336; sodium hydride; diisobutylaluminium hydride; In water; toluene; 1.1: Condensation / 2.1: Reduction / 3.1: Condensation / 4.1: Reduction / 5.1: Hydrolysis / 5.2: resolution;

DOI:10.1016/S0960-894X(99)00519-3

upstream raw materials:

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3S,5R,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoate

(±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

Downstream raw materials:

(3S,5R,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoic acid ,15-lactone

Refernces

• 1、 Hiyama,Reddy,Minami,Hanamoto. "Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors". . p. 350 - 363. Retrieved 2007/10/02.