(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester

Base Information

• Chemical Name: (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester
• CAS No.: 205647-21-8
• Molecular Formula: C₂₉H₄₄FNO₅SSi
• Molecular Weight: 565.822
• Mol file: 205647-21-8.mol

Synonyms:(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester

Chemical Property of (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester

There total 5 articles about (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl 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)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester (109721-08-6) → (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester (205647-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -30 - 2 °C

1.2: 100 percent / tetrahydrofuran; hexane / 0.92 h / -66 - -30 °C

2.1: 74 percent / triethylamine; methanesulfonyl chloride / CH₂Cl₂ / 0.92 h / 0 - 15 °C

3.1: 98 percent / methanol / 0.53 h / 0 °C

4.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

4.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

With n-butyllithium; potassium tert-butylate; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Cyclization / 3.1: Ring cleavage / 4.1: Metallation / 4.2: Condensation;

DOI:10.1021/jo9722156

Reference yield:

3-(4-fluoro-phenyl)-5-isopropyl-2-methyl-1H-pyrrole → (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester (205647-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CH₂Cl₂ / 1 h / Heating

2.1: CH₂Cl₂ / 0.5 h / 20 °C

3.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

3.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

With potassium tert-butylate; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 1.1: Alkylation / 2.1: Methylation / 3.1: Metallation / 3.2: Condensation;

DOI:10.1021/jo9722156

Reference yield:

(4R)-[(tert-butyldimethylsilyl)oxy]-6-[(methanesulfinyl)methylene]tetrahydropyran-2-one (148866-38-0) → (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester (205647-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / methanol / 0.53 h / 0 °C

2.1: t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0.25 h / 0 °C

2.2: 1.98 g / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 0 °C

With potassium tert-butylate; In tetrahydrofuran; methanol; tert-butyl alcohol; 1.1: Ring cleavage / 2.1: Metallation / 2.2: Condensation;

DOI:10.1021/jo9722156

upstream raw materials:

(S)-3-<(tert-butyldimethylsilyl)oxy>pentanedioic acid, monomethylester

(4R)-[(tert-butyldimethylsilyl)oxy]-6-[(methanesulfinyl)methylene]tetrahydropyran-2-one

[[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]methyl]dimethylamine

(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid

Downstream raw materials:

(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester

(E)-(R)-7-[4-(4-Fluoro-phenyl)-2-isopropyl-1-methanesulfonyl-5-methyl-1H-pyrrol-3-yl]-3-hydroxy-5-oxo-hept-6-enoic acid methyl ester

(3R,5S)-7-[4-(4-fluorophenyl)-2-isopropyl-1-(methanesulfonyl)-5-methyl-1H-pyrrol-3-yl]-3,5-dihydroxy-6-heptenoic acid methyl ester