953776-62-0

Basic information

• Product Name: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin
• Synonyms: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin;N-[4-(4-Fluorophenyl)-5-Methyl-6-(1-Methylethyl)-2-pyriMidinyl]-N-MethylMethanesulfonaMide
• CAS NO: 953776-62-0
• Molecular Formula: C₁₆H₂₀FN₃O₂S
• Molecular Weight: 337.4123032
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 953776-62-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 118 °C
• Boiling Point: 471.0±47.0 °C(Predicted)
• Appearance: /
• Density: 1.246±0.06 g/cm3(Predicted)
• PKA: 0.43±0.10(Predicted)
• CAS DataBase Reference: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin(953776-62-0)
• EPA Substance Registry System: 5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin(953776-62-0)

Safety Data

• Hazardous Substances Data: 953776-62-0(Hazardous Substances Data)

Usage

Description

5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin is a pyrimidine derivative and a key intermediate in the synthesis of Rosuvastatin, a widely used cholesterol-lowering drug. It possesses a unique chemical structure with a 5-methyl group and a 7-carboxy-3,5-dihydroxyhept-1-enyl moiety, which contribute to its potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin is used as a key intermediate in the synthesis of Rosuvastatin, a cholesterol-lowering drug. It plays a crucial role in the production of this medication, which helps in reducing the levels of low-density lipoprotein (LDL) cholesterol and triglycerides in the blood, thereby lowering the risk of cardiovascular diseases.
Used in Drug Development:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin can be used as a starting material for the development of new drugs with improved pharmacological properties. Its unique chemical structure allows for further modifications and optimization, potentially leading to the discovery of novel therapeutic agents with enhanced efficacy and safety profiles.
Used in Research and Development:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin can be employed as a research tool in the study of cholesterol metabolism and the development of new treatments for hypercholesterolemia and related conditions. Its unique structure and properties make it a valuable compound for investigating the mechanisms of action and potential applications of Rosuvastatin and its analogs.
Used in Chemical Synthesis:
5-Des-(7-carboxy-3,5-dihydroxyhept-1-enyl)-5-Methyl Rosuvastatin can be utilized in various chemical synthesis processes, such as the preparation of other pyrimidine derivatives or the development of new chemical compounds with potential applications in different industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 1068433-24-8 (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dihydroxymethyl)tetrahydro-2H-pyran-2-one 
• 1246665-81-5 C₂₈H₄₅FN₃O₂PS 
• 1207460-34-1 4-(4-fluorophenyl)-6-isopropyl-N,5-dimethylpyrimidin-2-amine 
• 124-63-0 methanesulfonyl chloride 
• 114433-94-2 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione 

Downstream Products

• 799842-07-2 N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 147118-37-4 N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide 
• 1416000-51-5 N-(5-(dibromomethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1416000-55-9 N-(5-(bromomethyl)-4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)pyrimidin-2-yl)-N-methylmethanesulfonamide 
• 1416000-58-2 N-(4-(2-bromopropan-2-yl)-6-(4-fluorophenyl)-5-methylpyrimidin-2-yl)-N-methylmethanesulfonamide 
• 289042-12-2 2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF KEY INTERMEDIATES FOR THE SYNTHESIS OF STATINS OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

Process for the preparation of key intermediates for the synthesis of statins or pharmaceutically acceptable salts thereof

The invention relates to commercially viable process for the synthesis of key intermediates for the preparation of statins, in particular Rosuvastatin and Pitavastatin or respective pharmaceutically acceptable salts thereof. A new simple and short synthetic route for key intermediates is presented which benefits from the use of cheap and readily available starting materials, by which the conventionally most frequently used DIBAL-H as reducing agent can be avoided.

Lactone pathway to statins utilizing the wittig reaction. the synthesis of rosuvastatin

The first entry to statins via lactonized side chain is reported, exemplified by the synthesis of rosuvastatin. The key step is Wittig coupling of (2S,4R)-4-(tert-butyldimethylsilyloxy)-6-oxotetrahydro-2H-pyran-2-carbaldehyde and phosphonium salt of an appropriately functionalized pyrimidine heterocy'le. One-pot deprotection and hydrolysis of the resulting 4-O-TBS rosuvastatin lactone provided rosuvastatin in high yield.