132127-34-5

Basic information

• Product Name: (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone
• Synonyms: (3R,4S)-3-HYDROXY-4-PHENYL-2-AZETIDINONE;(3r-cis)-3-hydroxy-4-phenyl-2-azetidinone;CIS-3-HYDROXY-4-PHENYL-2-AZETIDINONE;(3R,4S)-;(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one;(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone, >=99%
• CAS NO: 132127-34-5
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 1308068-626-2
• Product Categories: Chiral Reagents;CHIRAL CHEMICALS;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 132127-34-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 187-188°C
• Boiling Point: 430.414 °C at 760 mmHg
• Flash Point: 214.107 °C
• Appearance: White solid
• Density: 1.308
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.86±0.40(Predicted)
• CAS DataBase Reference: (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone(132127-34-5)
• EPA Substance Registry System: (3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone(132127-34-5)

Safety Data

• Hazardous Substances Data: 132127-34-5(Hazardous Substances Data)

Usage

Description

(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone is a chiral organic compound characterized by its unique four-membered azetidinone ring and a phenyl group attached to the fourth carbon. It is a white solid with specific stereochemistry, which is crucial for its potential applications.

Uses

Used in Pharmaceutical Industry:
(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone is used as an intermediate in the synthesis of various pharmaceutical compounds, particularly for the production of Docetaxel or Paclitaxel. These are important anticancer drugs that are widely used in the treatment of different types of cancers. The compound's specific stereochemistry and structural features make it a valuable building block in the development of these therapeutic agents.
Used in Chemical Research:
(3R,4S)-3-Hydroxy-4-phenyl-2-azetidinone is also used as a research compound in the field of organic chemistry. Its unique structure and properties make it an interesting subject for studying various chemical reactions and exploring its potential applications in the synthesis of other complex molecules. This can lead to the discovery of new drugs or materials with novel properties.

InChI:InChI=1/C9H9NO2/c11-8-7(10-9(8)12)6-4-2-1-3-5-6/h1-5,7-8,11H,(H,10,12)/t7-,8+/m0/s1

Upstream product

• 132127-31-2 (3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 
• 132127-31-2 3-Triisopropylsilyloxy-4-phenylazetidin-2-one 
• 144790-01-2 (3R-cis)-3-acetyloxy-4-phenyl-2-azetidinone 
• 130632-19-8 (-)-(3R,4S)-3-Benzyloxy-4-phenylazetidin-2-one 
• 132127-30-1 (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one 
• 950586-04-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 
• 950586-06-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-tert-butyldimethylsiloxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 
• 880781-88-4 (3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 100-52-7 benzaldehyde 
• 438566-59-7 (3R,4S)-cis-3-benzyloxy-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-phenylazetidin-2-one 
• 438566-45-1 (3R,4S)-3-benzyloxy-1-[(2S)-2-(1-ethyl-1-methoxypropyl)pyrrolidin-1-yl]-4-phenylazetidin-2-one 
• 208848-58-2 Acetic acid (3R,4S)-1-[(S)-1-(4-methoxy-phenyl)-propyl]-2-oxo-4-phenyl-azetidin-3-yl ester 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 

Downstream Products

• 149140-54-5 (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 156742-11-9 (3R,4S)-4-cyclohexyl-3-hydroxy-2-azetidinone 
• 201856-48-6 (3R,4S)-3-<((R^*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone 
• 160535-69-3 (3R-cis)-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 149249-91-2 (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone 
• 182155-36-8 (3R,4S)-3-hydroxy-3-methyl-4-phenyl-β-lactam 
• 182155-26-6 (S)-1-(tert-Butyl-dimethyl-silanyl)-4-phenyl-azetidine-2,3-dione 
• 182155-24-4 (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-4-phenyl-azetidin-2-one 
• 182155-28-8 (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-hydroxy-3-methyl-4-phenyl-azetidin-2-one 
• 182155-37-9 (3R,4S)-3-[(triethylsilyl)oxy]-4-(phenyl)-3-methyl-azetidinone 
• 182155-22-2 (3R,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-(1-methoxy-1-methyl-ethoxy)-4-phenyl-azetidin-2-one 
• 182155-38-0 (3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one 

Relevant articles and documents

A convenient synthesis of the paclitaxel side-chain via a diastereoselective Staudinger reaction

The N-benzylidene dexivative of (S)-(-)-1-(p-mathoxyphenyl)propyl-1- amine, obtained by a new resolution procedure, exhibits moderate selectivity in the reaction with 2-acetoxyketene; the (S)-(-)-1-(p-methoxyphenyl)propyl group can be oxidatively cleaved from the resultant β-lactam, an important precursor for taxane semi-synthesis.

Beta-lactam synthesis

The present invention is directed to a process for the preparation of β-lactams. Generally, an imine is cyclocondensed with a ketene acetal or enolate to form the β-lactam product in a "one pot" synthesis, this process is generally performed at a higher temperature than conventional processes.

N,N-dialkylhydrazones as the imine component in the Staudinger-like [2+2] cycloaddition to benzyloxyketene

To overcome the limitations of using unstable imines in Staudinger cycloadditions to ketenes, aldehyde N,N-dialkylhydrazones 1 were used as stable imines. This strategy and a fine tuning of the auxiliary result in a straightforward synthesis of cycloadducts 2, deprotected β-lactams 3, and isoserines 4 (see scheme: a) Et3N, toluene, Δ; b) 1. magnesium monoperoxyphthalate, 2. H2, Pd/C; c) H+).