Fluvastatin t-butyl ester, (-)-

Base Information

• Chemical Name: Fluvastatin t-butyl ester, (-)-
• CAS No.: 129332-29-2
• Molecular Formula: C₂₈H₃₄FNO₄
• Molecular Weight: 467.581
• Hs Code.: 2933997500
• European Community (EC) Number: 603-330-9
• UNII: 9M28SIF9WZ
• DSSTox Substance ID: DTXSID20173144
• Nikkaji Number: J884.017B
• Wikidata: Q27272723
• Mol file: 129332-29-2.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:

• Boiling Point: 642.264 °C at 760 mmHg
• PKA: 13.90±0.20(Predicted)
• Flash Point: 342.229 °C
• PSA: 71.69000
• Density: 1.139 g/cm³
• LogP: 5.88520
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (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:

99% ^*data from raw suppliers

tert-ButylFluvastatin ^*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: tert-Butyl Fluvastatin (Fluvastatin USP Related Compound B) is a derivative of Fluvastatin (F601250), a synthetic HMG-CoA reductase inhibitor. Antilipemic.

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

There total 23 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: 82.0%

((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3-hydroxy-5-oxo-6-heptenoic acid 1,1-dimethylethyl ester (194935-02-9) → S-((R*S*)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid 1,1-dimethylethyl ester (194935-03-0,129332-29-2)

Guidance literature:

With sodium tetrahydroborate; diethyl methoxy borane; In tetrahydrofuran; methanol; at -78 ℃; for 3h;

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

Reference yield: 80.0%

7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid-1,1-dimethylethyl ester (375846-25-6) → R*,S*-(E)-(+/-)-3,5-dihydroxy-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-6-heptenoic acid tert-butyl ester (129332-29-2)

Guidance literature:

7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-5-hydroxy-3-oxo-6-heptenoic acid-1,1-dimethylethyl ester; With sodium tetrahydroborate; diethylmethoxyborane; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;

With dihydrogen peroxide; In Isopropyl acetate; at 50 ℃; for 1h; Inert atmosphere;

DOI:10.1021/op060191b

Reference yield: 80.0%

(+/-)-erythro-(E)-7-[3-(4-fluoro-phenyl)-1-(1-methyl-ethyl)-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid t-butyl ester cyclic borane complex → (+/-)-erythro-(E)-7-[3-(4-fluoro-phenyl)-1-(1-methyl-ethyl)-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid t-butyl ester (129332-29-2)

Guidance literature:

With dihydrogen peroxide; In water; ethyl acetate; at 15 - 25 ℃; for 20h;

upstream raw materials:

((S)-(E))-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3-hydroxy-5-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

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

Refernces

• 1、 Fuenfschilling, Peter C.,Hoehn, Pascale,Mutz, Jean-Paul. "An Improved Manufacturing Process for Fluvastatin". . p. 13 - 18. Retrieved 2012/12/26.
• 2、 -. "PROCESS FOR PREPARATION OF STATINS WITH HIGH SYN TO ANTI RATIO". Page/Page column 15. . Retrieved 2008/06/13.