953805-20-4

Basic information

• Product Name: (S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one
• Synonyms: (S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one
• CAS NO: 953805-20-4
• Molecular Formula: C₂₅H₂₈FNO₅
• Molecular Weight: 441.4919232
• Mol File: 953805-20-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one(953805-20-4)
• EPA Substance Registry System: (S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one(953805-20-4)

Safety Data

• Hazardous Substances Data: 953805-20-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one is used as an intermediate in the synthesis of (3’R,3R,4R)-Ezetimibe (E974990), a structural analog of Ezetimibe (E975000). Ezetimibe is an antihyperlipoproteinemic agent and a cholesterol absorption inhibitor, which helps in the management of high cholesterol levels and related health issues. (S)-3-(4-(2-(4-fluorophenyl)-5,5-diMethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one's unique structure allows it to be a key component in the development of these medications, contributing to their efficacy and therapeutic potential.

Upstream product

• 953805-21-5 4-(2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl)butanoic acid 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 462-06-6 fluorobenzene 
• 108-55-4 glutaric anhydride, 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 189028-93-1 (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 

Downstream Products

• 953805-22-6 3-{(2R,3S)-3-[(4-fluorophenyl)amino]-2-[2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]-3-[4-(benzyloxy)phenyI]propanoyl}-(4S)-4-phenyl-1,3-oxazolidin-2-one 
• 953805-23-7 3-{(2R,3S)-3-[(4-fluorophenyl)amino]-2-[2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]-3-[4-(trimethylsilanyloxy)phenyl]propanoyl}-(4S)-4-phenyl-1,3-oxazolidin-2-one. 
• 1478664-18-4 (3R,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1478663-95-4 (S)-3-((R)-2-((S)-(4-((tert-butyldimethylsilyl)oxy)phenyl)((4-fluorophenyl)amino)methyl)-4-(2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one 
• 1478663-95-4 (S)-3-((R)-2-((R)-(4-((tert-butyldimethylsilyl)oxy)phenyl)((4-fluorophenyl)amino)methyl)-4-(2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one 
• 953805-24-8 4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-3(R)-{2-[2-(4-fluorophenyI)-5,5-dimethyl-[1,3]-dioxan-2-yl]-ethyl}azetidine-2-one 
• 190595-65-4 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 
• 163222-32-0 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone 
• 163222-33-1 ezetemibe 

Relevant articles and documents

Ezetimibe intermediate, synthesis method of intermediate and synthesis method of ezetimibe

The invention provides an ezetimibe intermediate, a synthesis method of the intermediate and a synthesis method of ezetimibe. The method is short in synthetic route. The method includes the steps of making fluorobenzene as the initial raw material sequentially have acylation reaction with glutaric anhydride and 4(S)-4-phenyl oxazolidinone to generate a compound II, protecting carbonyl through 2,2-bis-substituted-1,3-propylene glycol to obtain a compound III, generating a compound V through the compound III and a compound IV under the catalysis of titanium tetrachloride, cyclizing the compound V to generate a compound VI, hydrolyzing the compound VI to obtain a compound VII, and reducing the compound VII through a borane chiral reducing agent and removing a benzyl protecting group in a hydrogenated mode to obtain the ezetimibe. The method is high in yield, little in side reaction and suitable for industrial mass production.

First synthesis and characterization of SRR/RSS-Ezetimibe

The two stereoisomers, SRR-Ezetimibe 2 and RSS-Ezetimibe 3 are related substances of the cholesterol absorption inhibitor drug Ezetimibe 1. Herein, we present an efficient and practical synthesis approach to deliver these two stereoisomers for the first t

PROCESSES FOR THE SYNTHESIS OF AZETIDINONE

Provided are intermediates useful for the synthesis of hydroxyl-alkyl substituted azetidinones, processes of their preparation, and processes for the synthesis of certain hydroxyl-alkyl substituted azetidinones. Also provided are processes for the synthesis ofl-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)- hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone, or ezetimibe.