221349-56-0

Basic information

• Product Name: (3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one
• Synonyms: (3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one
• CAS NO: 221349-56-0
• Molecular Formula: C₂₄H₂₂FNO₄
• Molecular Weight: 407.4341832
• Mol File: 221349-56-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one(221349-56-0)
• EPA Substance Registry System: (3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one(221349-56-0)

Safety Data

• Hazardous Substances Data: 221349-56-0(Hazardous Substances Data)

Usage

Description

(3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one is a complex organic compound characterized by its unique molecular structure. It is a chiral molecule with specific stereochemistry at the 3rd and 4th carbon positions (3S,4S). The compound features a benzyloxy-phenyl group, a 1,2-dihydroxyethyl group, and a 4-fluorophenyl group attached to its azetidinone core. This structural diversity suggests potential applications in various fields, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
(3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one is used as a reactant in the synthesis of Sch 57939, a β-lactam-based cholesterol absorption inhibitor. This application is due to its structural compatibility with the target molecule, allowing for the creation of a compound with potential therapeutic benefits in managing cholesterol levels.
Used in Chemical Synthesis:
In the chemical synthesis industry, (3S,4S)-4-(4-(Benzyloxy)phenyl)-3-((S)-1,2-dihydroxyethyl)-1-(4-fluorophenyl)azetidin-2-one can be utilized as a building block or intermediate for the development of other complex organic molecules. Its unique functional groups and stereochemistry make it a valuable component in the synthesis of various pharmaceuticals, agrochemicals, or specialty chemicals.

Upstream product

• 5469-16-9 (3S)-hydroxy-γ-butyrolactone 
• 70627-52-0 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine 

Downstream Products

• 221349-58-2 (2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde 
• 191330-56-0 [14C]-Sch 57871 
• 190595-65-4 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 
• 163222-33-1 ezetemibe 
• 163222-32-0 (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone 
• 221349-60-6 (3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one 
• 231301-00-1 (3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one 

Relevant articles and documents

A concise asymmetric synthesis of A β-lactam-based cholesterol absorption inhibitor

A concise, four-step, asymmetric synthesis of β-lactam-based cholesterol absorption inhibitor, Sch 57939, was developed. The discovery of a one-step enantio- and diastereoselective synthesis of a trans-β-lactam provided easy access to the desired three chiral centers. A novel zinc phenoxide-promoted ether synthesis was reported for the completion of the side chain.