154306-81-7

Basic information

• Product Name: (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one
• CAS NO: 154306-81-7
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.32
• Mol File: 154306-81-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 481.2°C at 760 mmHg
• Flash Point: 244.8°C
• Density: 1.241g/cm³
• Vapor Pressure: 4.55E-10mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one(154306-81-7)
• EPA Substance Registry System: (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one(154306-81-7)

Safety Data

• Hazardous Substances Data: 154306-81-7(Hazardous Substances Data)

Usage

General Description

The chemical (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one, also known as (3R,4S)-(+)-cis-4-phenyl-3-(1-phenylethyl)azetidin-2-one, is a chiral azetidinone compound. It is used in organic synthesis as a building block for the preparation of various pharmaceuticals and biologically active compounds. The chemical's stereochemistry and functional groups make it a versatile intermediate for the synthesis of diverse molecules. It may also have potential pharmacological and biochemical applications due to its structural and stereochemical properties.

Upstream product

• 212764-79-9 methyl (2R,3S)-2-methoxy-3-phenyl-3-<(S)-methylbenzylamino>propanoate 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 212764-84-6 (3R,4S)-3-methoxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one 

Downstream Products

• 147058-27-3 methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 

Relevant articles and documents

Practical synthesis of taxol side chain

Practical large scale synthesis of N-benzoyl-(2R,3S)-phenylisoserine methyl ester of the Taxol side chain has been attained from the coupling of chiral imine of N-[(S)-methylbenzyl]benzaldimine with (Z)-α-methoxy trimethylsilyl ketene acetal followed by the sequential reactions of lactamization, demethylation, methanolysis and N-benzoylation.

Method for the preparation of β-phenylisoserine derivatives

Method for the preparation of β-phenylisoserine derivatives of general formula (I) involving the action of an anhydride and hydrogen with a product of general formula (II). The products of general formula (I) are especially useful in the preparation of taxoids having outstanding antitumour properties. In general formulae (I) and (II), Ar is an aryl radical, Ph is a phenyl radical or an optionally substituted α or β-naphtyl, R is a hydrogen atom or an alkyl radical optionally substituted by a phenyl radical and R1 is an optionally substituted phenyl radical or a R2 --O radical wherein R2 is an alkyl, alkenyl, cycloalkyl, phenyl or heterocyclyl. STR1