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

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

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 3-Triisopropylsilyloxy-4-phenylazetidin-2-one 
• 132127-30-1 (3R,4S)-3-<(tert-butyldimethylsilyl)oxy>-4-phenylazetidin-2-one 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 100-52-7 benzaldehyde 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 
• 206447-91-8 N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionamide 
• 206447-89-4 N-(p-methoxyphenyl) (2R,3S)-2,3-dihydroxy-3-phenylpropionamide 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 438566-45-1 (3R,4S)-3-benzyloxy-1-[(2S)-2-(1-ethyl-1-methoxypropyl)pyrrolidin-1-yl]-4-phenylazetidin-2-one 
• 438566-59-7 (3R,4S)-cis-3-benzyloxy-1-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]-4-phenylazetidin-2-one 
• 880781-88-4 (3R,4S)-3-tert-butyldimethylsiloxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 950586-06-8 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-tert-butyldimethylsiloxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 
• 950586-04-6 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 

Downstream Products

• 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 
• 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 
• 182155-39-1 (3R,4S)-1-tert-butoxycarbonyl-3-[(triethylsilyl)oxy]-4-(phenyl)-3-methylazetidinone 
• 160084-30-0 (3R,4S)-1-Cyclohexanecarbonyl-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.

Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation

Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivit

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.

Studies on stereoselective [2+2] cycloadditions between N,N-dialkylhydrazones and ketenes

Staudinger-like cycloadditions between chiral, non-racemic N,N-dialkylhydrazones 1 and functionalized ketenes constitute an efficient methodology for the stereoselective construction of the β-lactam ring. The potential for fine tuning of the dialkylamino

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+).

β-lactams, methods for the preparation of taxanes, and sidechain-bearing taxanes

Novel β-lactams finding utility as intermediates in the preparation of sidechain-bearing taxanes such as taxol and taxol derivatives. The present invention also relates to novel methods of coupling β-lactams to form such sidechain-bearing taxanes, and to novel sidechain-bearing taxanes.

β-lactams, methods for the preparation of taxanes, and sidechain-bearing taxanes

Novel β-lactams finding utility as intermediates in the preparation of sidechain-bearing taxanes such as taxol and taxol derivatives. The present invention also relates to novel methods of coupling β-lactams to form such sidechain-bearing taxanes, and to

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one, an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo- 3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation.

Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment

The present invention is directed to novel taxanes useful as chemotherapeutic agents or their precursors. Processes for preparing the novel taxanes include coupling reactions, in the presence of a base, of baccatin of formula (III) or (IV) STR1 with β-lac

Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment

The present invention is directed to novel taxanes useful as chemotherapeutic agents or their precursors. Processes for preparing the novel taxanes include coupling reactions, in the presence of a base, of baccatin of formula (III) or (IV) STR1 with β-lac