131466-61-0

Basic information

• Product Name: (3R)-3-(tert-ButyldiMethylsilyloxy)glutaric acid -1-((R)-(-)-Mandelic acid ester
• Synonyms: (3R)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]pentanedioic acid 1-[(R)-carboxyphenylmethyl] ester;(3R)-3-(tert-ButyldiMethylsilyloxy)glutaric acid -1-((R)-(-)-Mandelic acid ester
• CAS NO: 131466-61-0
• Molecular Formula: C₁₉H₂₈O₇Si
• Molecular Weight: 396.50692
• Mol File: 131466-61-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R)-3-(tert-ButyldiMethylsilyloxy)glutaric acid -1-((R)-(-)-Mandelic acid ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-3-(tert-ButyldiMethylsilyloxy)glutaric acid -1-((R)-(-)-Mandelic acid ester(131466-61-0)
• EPA Substance Registry System: (3R)-3-(tert-ButyldiMethylsilyloxy)glutaric acid -1-((R)-(-)-Mandelic acid ester(131466-61-0)

Safety Data

• Hazardous Substances Data: 131466-61-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3R)-3-(tert-Butyldimethylsilyloxy)glutaric acid -1-((R)-(-)-mandelic acid ester is used as a key intermediate for the synthesis of complex organic molecules. Its unique functional groups facilitate various chemical reactions, enabling the construction of a wide range of organic compounds with potential applications in different industries.
Used in Medicinal Chemistry:
In the pharmaceutical industry, (3R)-3-(tert-Butyldimethylsilyloxy)glutaric acid -1-((R)-(-)-mandelic acid ester is utilized as a building block for the development of new drugs. Its functional groups can be modified to create bioactive molecules with potential therapeutic effects. (3R)-3-(tert-Butyldimethylsilyloxy)glutaric acid -1-((R)-(-)-mandelic acid ester's versatility allows for the design of drugs targeting specific diseases or conditions, contributing to the advancement of medicinal chemistry.
Used in Chemical Research:
(3R)-3-(tert-Butyldimethylsilyloxy)glutaric acid -1-((R)-(-)-mandelic acid ester serves as a valuable research tool in chemical studies. Its unique structure and functional groups provide insights into the reactivity and behavior of complex organic molecules. Researchers can use (3R)-3-(tert-Butyldimethylsilyloxy)glutaric acid -1-((R)-(-)-mandelic acid ester to explore new reaction pathways, develop innovative synthetic methods, and gain a deeper understanding of organic chemistry.
Used in Material Science:
In the field of material science, (3R)-3-(tert-Butyldimethylsilyloxy)glutaric acid -1-((R)-(-)-mandelic acid ester can be employed as a component in the development of novel materials with specific properties. Its functional groups can be incorporated into polymers, coatings, or other materials to impart desired characteristics, such as improved stability, enhanced reactivity, or tailored interactions with other molecules.

Upstream product

• 32328-03-3 diethyl 3-hydroxyglutarate 
• 91424-39-4 3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid,diethyl ester 
• 91424-40-7 3-(tert-butyldimethylsilyloxy)glutaric anhydride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 97415-09-3 (R)-benzyl 2-hydroxy-2-phenyl-acetate 
• 10606-72-1 (R)-mandelic acid ethyl ester 

Downstream Products

• 147118-35-2 methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate 
• 147118-39-6 methyl (3R,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate 
• 1350364-05-4 hydrogen (3R)-1-methyl 3-[(tert-butyldimethylsilyl)-oxy]pentanedioate benzylamine salt 
• 1350364-18-9 C₁₅H₂₈O₇Si 
• 182075-76-9 (R,E)-methyl 3-(tert-butyldimethylsilyloxy)-7-(2-cyclopropyl-4-(-4-fluorophenyl)-quinolin-3-yl)-5-oxohept-6-enoate 
• 917752-45-5 methyl (E)-7-[2-cyclopropyl-4-(4-flurophenyl)-3-quinolinyl]-3-hydroxy-5-oxo-6-heptenate 
• 109744-49-2 Hydrogen (3R)-1-methyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate 

Relevant articles and documents

Preparation method of high-purity statin drug intermediate

The invention relates to a preparation method of a high-purity statin drug intermediate. The preparation method is characterized in that 3-hydroxyl ethyl glutarate is used as the initial raw material to prepare (3R)-tert-butyl dimethyl silyloxy-5-oxo-6-triphenyl phosphine caproate (abbreviated as J6) through substitution reaction, hydrolysis reaction, cyclization reaction, resolution reaction, hydrogenation reaction, acylation reaction and Wittig reaction. The preparation method is mild in condition, stable in process, cheap in raw material, easy in raw material obtaining, easy in three-waste treatment, low in preparation cost, high in product purity and suitable for industrial production.

A synthetic method of the compound

The invention relates to the field of chemistry and in particular relates to the field of medical chemistry. The invention aims to find a novel synthetic route suitable for Vb compounds in industrial production and adaptively provides a specific implementation process of the novel synthetic route, so that high-purity low-cost Vb compounds can be obtained. The compound Vb is prepared by taking a compound I as an initial raw material, so that the traditional Vb synthetic process is replaced. With the adoption of the synthetic route disclosed by the invention, the invention has the advantages that 1, dangerous and expensive butyl lithium is not used; 2, hydrogenation is avoided, and expensive metal palladium is avoided; and 3, more important, debenzylation byproducts in the hydrogenation are avoided. Meanwhile, because the price of the compound I is low, after the synthetic route disclosed by the invention is adopted, the industrial production need of the obtained high-purity low-cost compound V can be met.

AN IMPROVED PROCESS FOR THE PREPARATION OF AN INTERMEDIATE OF HMG-COA REDUCTASE INHIBITORS

The present invention relates to an improved process for the preparation of intermediates of HMG-CoA reductase inhibitors of Formulae-IXa or IXb and further conversion to HMG-CoA reductase inhibitors and pharmaceutically acceptable salts thereof.

Practical synthesis of chiral synthons for the preparation of HMG-CoA reductase inhibitors

A practical procedure for the enantioselective preparation of optically pure (R)- and (S)-monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid has been developed by diastereoselective ring-opening of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic anhydride 5 by benzyl (R)- and (S)-mandelate, respectively. These half-esters afforded chiral Wittig reagent 2 and Horner-Wadsworth-Emmons (HWE) reagent 1 efficiently which have been proved to be useful in the synthesis of HMG-CoA reductase inhibitors. The method is applied to the synthesis of the (R)-3-methylglutaric acid, monomethyl ester.