(4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester

Base Information

• Chemical Name: (4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester
• CAS No.: 500731-91-9
• Molecular Formula: C31H38FNO4
• Molecular Weight: 507.64
• Mol file: 500731-91-9.mol

Synonyms:(3R,5S)-Fluvastatin-3,5-acetonide tert-Butyl Ester;(4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester

Chemical Property of (4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 608.734°C at 760 mmHg
• Flash Point: 321.951°C
• PSA: 49.69000
• Density: 1.123g/cm³
• LogP: 7.68350
• Storage Temp.: Refrigerator
• Solubility.: Acetone, Diethyl Ether, Ethyl Acetate

Purity/Quality:

99%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate for the preparation of (3R,5S)-Fluvastatin.

Technology Process of (4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester

There total 7 articles about (4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl 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: 65.8%

((3-(4-fluorophenyl)-1-isopropylindol-2-yl)methyl)diphenylphosphine oxide + tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) → tert-butyl 2-((4R,6S)-6-((E)-2-(3-(4-fluorophenyl)-1-isopropylindol-2-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (500731-91-9)

Guidance literature:

((3-(4-fluorophenyl)-1-isopropylindol-2-yl)methyl)diphenylphosphine oxide; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 20 ℃; for 0.0833333h; Inert atmosphere;

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate; In tetrahydrofuran; at -78 - 0 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jacs.5b10119

Reference yield:

C26H24FN3O2S + tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (124752-23-4) → tert-butyl 2-((4R,6S)-6-((E)-2-(3-(4-fluorophenyl)-1-isopropylindol-2-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (500731-91-9)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 25 - 35 ℃; for 3h;

Reference yield:

3-(4'-fluorophenyl)-1-(1'-methylethyl)-1H-indole (93957-49-4) → tert-butyl 2-((4R,6S)-6-((E)-2-(3-(4-fluorophenyl)-1-isopropylindol-2-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (500731-91-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trichlorophosphate / 0.25 h / 20 °C / Inert atmosphere

1.2: 2 h / 80 °C / Inert atmosphere

2.1: sodium tetrahydroborate / ethanol / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: phosphorus tribromide / toluene / 2.5 h / 0 - 20 °C / Inert atmosphere

4.1: toluene / 5 h / 120 °C / Inert atmosphere

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.08 h / -78 - 20 °C / Inert atmosphere

5.2: 12 h / -78 - 0 °C / Inert atmosphere

With sodium tetrahydroborate; phosphorus tribromide; potassium hexamethylsilazane; trichlorophosphate; In tetrahydrofuran; ethanol; toluene;

DOI:10.1021/jacs.5b10119

upstream raw materials:

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

3-(4'-fluorophenyl)-1-(1'-methylethyl)-1H-indole

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carboxaldehyde

Refernces

• 1、 -. "NOVEL PROCESS FOR STATINS AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF". Page/Page column 55; 73. . Retrieved 2008/06/13.