477558-79-5

Basic information

• Product Name: 3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)-
• Synonyms: 3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)-;Methyl-5-oxo-5-((4S)-2-oxo-4-phenyl-1,3-oxazolidin-3yl) pentanoate;(4S)-delta,2-Dioxo-4-phenyl-3-oxazolidinepentanoic acid methyl ester;d,2-dioxo-4-phenyl-,Methyl ester,(4S)-3-Oxazolidinepentanoic acid;(S)-Methyl 5-oxo-5-(2-oxo-4-phenyloxazolidin-3-yl)pentanoate;Methyl d,2-Dioxo-(S)-4-Ph-3-oxazolidinepentanoate
• CAS NO: 477558-79-5
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 291.29918
• Mol File: 477558-79-5.mol

Chemical Properties

• Boiling Point: 474.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.254±0.06 g/cm3 (20 ºC 760 Torr)
• PKA: -3.12±0.40(Predicted)
• CAS DataBase Reference: 3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)-(477558-79-5)
• EPA Substance Registry System: 3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)-(477558-79-5)

Safety Data

• Hazardous Substances Data: 477558-79-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)is used as a building block in organic synthesis for the preparation of various bioactive compounds. Its unique structure and chirality make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)is utilized as a key intermediate in the development of new drugs. Its specific stereochemistry allows for the creation of enantiomerically pure compounds, which is essential for achieving desired therapeutic effects and minimizing side effects.
Used in Chiral Chemistry:
3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)is employed in chiral chemistry for the synthesis of enantiomerically pure compounds. Its chiral center at the 4th position allows for the selective formation of specific enantiomers, which is crucial in various chemical reactions and applications.
Used in Drug Development:
3-Oxazolidinepentanoic acid,d,2-dioxo-4-phenyl-,Methyl ester,(4S)is used in drug development as a precursor for the synthesis of pharmaceutical compounds. Its unique structure and chirality enable the creation of novel drugs with improved efficacy, selectivity, and reduced side effects.

Upstream product

• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 1501-27-5 Pentanedioic acid, monomethyl ester 
• 108-55-4 glutaric anhydride, 

Downstream Products

• 934245-17-7 3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one 
• 917392-16-6 N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one 
• 1148132-74-4 (3R,4S)-N-(4-methylphenyl)-3-(3-[2-oxo-4-(4-methoxyphenyl)-1-(4-methoxyphenyl)-azetidinyl])propanamide 
• 1352878-41-1 C₂₈H₂₈N₂O₄ 
• 1352879-84-5 C₃₀H₃₀N₂O₇ 

Relevant articles and documents

Azetidinone derivatives and its preparation method and application

The invention discloses azacyclobutanone derivatives which are compounds as shown in the formula (I) and medicinal salts thereof. The invention further discloses a preparation method and application of the azacyclobutanone derivatives. The azacyclobutanone derivatives disclosed by the invention can be used for treating or preventing atherosclerosis or lowering plasma cholesterol level, and has strong plasma cholesterol reducing activity and wide market prospect.

Synthesis and biological evaluation of Ezetimibe analogs as possible cholesterol absorption inhibitors

In order to investigate the SAR of Ezetimibe analogs for cholesterol absorption inhibitions, amide group and electron-deficient pyridine ring were introduced to the C-(3) carbon chain of Ezetimibe. Eight new derivatives of the 2- azetidinone cholesterol absorption inhibitors have been synthesized, and all of them were enantiomerically pure. All the new compounds were evaluated for their activity to inhibit cholesterol absorption in hamsters, and most of them showed comparable effects in lowering the levels of total cholesterol in the serum.

An improved and scalable process for the synthesis of ezetimibe: An antihypercholesterolemia drug

An efficient, cost-effective and large-scale synthesis of ezetimibe 1, an antihypercholesterolemia drug, is described. Chiral oxazolidinone chemistry was used to fix the required stereochemistry of the β-lactam ring, and the chiral oxazaborolidine chemistry was used to fix the hydroxyl group stereochemistry. The synthesis significantly lowers the cost and provides easy access to ezetimibe on large scale.

2-Azetidinone derivatives: Design, synthesis and evaluation of cholesterol absorption inhibitors

Fourteen new derivatives of the 2-azetidinone cholesterol absorption inhibitors have been synthesized, and three of them were enantiomerically pure. All the new compounds were evaluated for their activity to inhibit cholesterol absorption in rats, and most of them showed comparable effects in lowering the levels of total cholesterol in the serum.

PREPARATION OF EZETIMIBE

A process for preparing ezetimibe.

Combinations of lipid modulating agents and substituted azetidinones and treatments for vascular conditions

The present invention provides compositions, therapeutic combinations and methods including: (a) at least one lipid modulating agent; and (b) at least one substituted azetidinone or substituted β-lactam sterol absorption inhibitor which can be useful for treating vascular conditions, diabetes, obesity and lowering plasma levels of sterols or 5α-stanols.