(3S,5S)-Atorvastatin Acetonide tert-Butyl Ester

Base Information

• Chemical Name: (3S,5S)-Atorvastatin Acetonide tert-Butyl Ester
• CAS No.: 472967-95-6
• Molecular Formula: C40H47FN2O5
• Molecular Weight: 654.822
• DSSTox Substance ID: DTXSID30468497
• Wikidata: Q82295716
• Mol file: 472967-95-6.mol

Synonyms:(3S,5S)-Atorvastatin Acetonide tert-Butyl Ester;472967-95-6;tert-butyl 2-[(4S,6S)-6-[2-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;SCHEMBL17987930;DTXSID30468497;tert-Butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenyl-caramoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;AKOS030240639

Chemical Property of (3S,5S)-Atorvastatin Acetonide tert-Butyl Ester

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 52-55°C
• Refractive Index: 1.569
• Boiling Point: 678.035 °C at 760 mmHg
• Flash Point: 363.863 °C
• PSA: 78.79000
• Density: 1.15 g/cm³
• LogP: 9.44200
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 654.34690077
• Heavy Atom Count: 48
• Complexity: 1040

Purity/Quality:

NLT 98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=C(N1CCC2CC(OC(O2)(C)C)CC(=O)OC(C)(C)C)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@H]2C[C@H](OC(O2)(C)C)CC(=O)OC(C)(C)C)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5
• Uses: An intermediate for the preparation of (3S,5S)-Atorvastatin

Technology Process of (3S,5S)-Atorvastatin Acetonide tert-Butyl Ester

There total 5 articles about (3S,5S)-Atorvastatin Acetonide tert-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:

tert-butyl (4S,6S)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate (947586-93-8) + 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide (125971-96-2,125971-58-6) → tert-butyl (4S,6S)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (472967-95-6)

Guidance literature:

With Trimethylacetic acid; In n-heptane; toluene; for 19h; Heating;

DOI:10.1135/cccc20080229

Reference yield:

Methyl 4-methyl-3-oxopentanoate (42558-54-3) → tert-butyl (4S,6S)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (472967-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1: ethylenediamine / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 140 - 150 °C / Inert atmosphere

2: glycine; acetic acid / n-heptane / 8 h / Inert atmosphere; Reflux

3: 10 h / 20 °C / Inert atmosphere

4: Trimethylacetic acid / toluene / 10 h / 100 - 110 °C / Inert atmosphere

With acetic acid; ethylenediamine; glycine; Trimethylacetic acid; In 5,5-dimethyl-1,3-cyclohexadiene; n-heptane; toluene;

Reference yield:

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → tert-butyl (4S,6S)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (472967-95-6)

Guidance literature:

Multi-step reaction with 3 steps

1: glycine; acetic acid / n-heptane / 8 h / Inert atmosphere; Reflux

2: 10 h / 20 °C / Inert atmosphere

3: Trimethylacetic acid / toluene / 10 h / 100 - 110 °C / Inert atmosphere

With acetic acid; glycine; Trimethylacetic acid; In n-heptane; toluene;

upstream raw materials:

tert-butyl (4S,6S)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Methyl 4-methyl-3-oxopentanoate

4-methyl-3-oxo-N-phenylpentanamide

Downstream raw materials:

(-)-Atorvastatin

atorvastatin sodium