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

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

Uses

Used in Pharmaceutical Synthesis:
(3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one is used as a building block in the pharmaceutical industry for the synthesis of various drugs and biologically active compounds. Its unique stereochemistry and functional groups enable the creation of diverse molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one is used as a versatile intermediate for the preparation of a wide range of molecules. Its structural and stereochemical properties make it a valuable component in the development of new chemical entities with potential applications in various industries.
Used in Research and Development:
(3R,4S)-3-hydroxy-4-phenyl-1-[(1S)-1-phenylethyl]azetidin-2-one is also used in research and development for the exploration of its potential pharmacological and biochemical applications. Its unique properties make it an interesting candidate for further study and development in the fields of medicine and biotechnology.

Upstream product

• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 212764-79-9 methyl (2R,3S)-2-methoxy-3-phenyl-3-<(S)-methylbenzylamino>propanoate 
• 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 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 

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.

Process for the preparation of β-phenylisoserine and its analogues

This invention relates to a method for preparing β-phenylisoserine and analogues thereof having general formula (I) STR1 from an aromatic aldehyde and an α-methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of g

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

A Practical Access to Chiral Phenylisoserinates, Preparation of Taxotere Analogs

A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using α-methyl-benzylamine as the chiral template of a Staudinger reaction.Optically pure diastereoisomers 6a-c were easily recovered by crystallization.After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium.Phenylisoserinates 8b,c were used to prepare analogs of Taxotere.