Fluvastatin t-butyl ester, (-)-

Base Information

• Chemical Name: Fluvastatin t-butyl ester, (-)-
• CAS No.: 194934-96-8
• Molecular Formula: C28H34FNO4
• Molecular Weight: 467.581
• European Community (EC) Number: 603-330-9
• UNII: 9M28SIF9WZ
• DSSTox Substance ID: DTXSID20173144
• Nikkaji Number: J884.017B
• Wikidata: Q27272723
• Mol file: 194934-96-8.mol

Synonyms:194934-96-8;Fluvastatin t-butyl ester, (-)-;(3R,5S)-Fluvastatin tert-Butyl Ester;tert-butyl (E,3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate;UNII-9M28SIF9WZ;9M28SIF9WZ;SCHEMBL556017;SCHEMBL556712;(-)-fluvastatin t-butyl ester;DTXSID20173144;1,1-Dimethylethyl (3RS,5SR,6E)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate (Fluvastatin tert-Butyl Ester);129332-29-2;AKOS025402058;CS-0165204;FLUVASTATIN SODIUM IMPURITY B [EP IMPURITY];J-012625;Q27272723;(3R,5S,6E)-3,5-Dihydroxy-7-[1-isopropyl-3-(4-fluorophenyl)-1H-indol-2-yl]-6-heptenoic acid tert-butyl ester;(3R,5S,6E)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic Acid 1,1-Dimethylethyl Ester? (Fluvastatin Impurity pound(c);1,1-DIMETHYLETHYL (3R,5S,6E)-7-(3-(4-FLUOROPHENYL)-1-(1-METHYLETHYL)-1H-INDOL-2-YL)-3,5-DIHYDROXYHEPT-6-ENOATE;6-HEPTENOIC ACID, 7-(3-(4-FLUOROPHENYL)-1-(1-METHYLETHYL)-1H-INDOL-2-YL)-3,5-DIHYDROXY-, 1,1-DIMETHYLETHYL ESTER, (3R,5S,6E)-;6-HEPTENOIC ACID, 7-(3-(4-FLUOROPHENYL)-1-(1-METHYLETHYL)-1H-INDOL-2-YL)-3,5-DIHYDROXY-, 1,1-DIMETHYLETHYL ESTER, (S-(R*,S*-(E)))-;tert-butyl (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate;tert-Butyl(E)-3,5-dihydroxy-7-[3'-(4''-fluorophenyl)-1'-methylethylindol-2'-yl)hept-6-enoate

Chemical Property of Fluvastatin t-butyl ester, (-)-

Chemical Property:

• Appearance/Colour: white solid
• Boiling Point: 642.264 °C at 760 mmHg
• PKA: 13.90±0.20(Predicted)
• Flash Point: 342.229 °C
• PSA: 71.69000
• Density: 1.13 g/cm³
• LogP: 5.88520
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly),Methanol (Slightly)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 467.24718673
• Heavy Atom Count: 34
• Complexity: 682

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3R,5S)-Fluvastatintert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N1C2=CC=CC=C2C(=C1C=CC(CC(CC(=O)OC(C)(C)C)O)O)C3=CC=C(C=C3)F
• Isomeric SMILES: CC(C)N1C2=CC=CC=C2C(=C1/C=C/[C@H](C[C@H](CC(=O)OC(C)(C)C)O)O)C3=CC=C(C=C3)F
• Uses: (3R,5S)-Fluvastatin tert-Butyl Ester (Fluvastatin EP Impurity B) is an intermediate for the preparation of (3R,5S)-Fluvastatin. An intermediate for the preparation of (3R,5S)-Fluvastatin

Technology Process of Fluvastatin t-butyl ester, (-)-

There total 3 articles about Fluvastatin t-butyl ester, (-)- 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:

((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid 1,1-dimethylethyl ester (194934-95-7) → (E)-(3R,5S)-(+)-7-[3-(4-fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid 1,1-dimethylethyl ester (194934-96-8,129332-29-2)

Guidance literature:

With sodium tetrahydroborate; diethyl methoxy borane; dihydrogen peroxide; sodium hydrogencarbonate; Yield given. Multistep reaction; 1.) THF, MeOH, -78 deg C, 1.5 h, 2.) THF, MeOH, ethyl acetate, room temperature, 15 h;

DOI:10.1016/S0040-4020(97)00686-8

Reference yield:

acetic acid tert-butyl ester (540-88-5) → (E)-(3R,5S)-(+)-7-[3-(4-fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid 1,1-dimethylethyl ester (194934-96-8,129332-29-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) NaBH₄, Et₂BOMe, 2.) aq. NaHCO₃, H₂O₂ / 1.) THF, MeOH, -78 deg C, 1.5 h, 2.) THF, MeOH, ethyl acetate, room temperature, 15 h

With sodium tetrahydroborate; diethyl methoxy borane; dihydrogen peroxide; sodium hydrogencarbonate;

DOI:10.1016/S0040-4020(97)00686-8

Reference yield:

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal (93957-50-7) → (E)-(3R,5S)-(+)-7-[3-(4-fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid 1,1-dimethylethyl ester (194934-96-8,129332-29-2)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) NaBH₄, Et₂BOMe, 2.) aq. NaHCO₃, H₂O₂ / 1.) THF, MeOH, -78 deg C, 1.5 h, 2.) THF, MeOH, ethyl acetate, room temperature, 15 h

With sodium tetrahydroborate; diethyl methoxy borane; dihydrogen peroxide; sodium hydrogencarbonate;

DOI:10.1016/S0040-4020(97)00686-8

upstream raw materials:

((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid 1,1-dimethylethyl ester

acetic acid tert-butyl ester

3-<3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl>-2(E)-propenal

Downstream raw materials:

R-((R*R*)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid 1,1-dimethylethyl ester

((R)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3-hydroxy-5-oxo-6-heptenoic acid 1,1-dimethylethyl ester

fluvastatin sodium

Refernces