201856-48-6

Basic information

• Product Name: (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone
• Synonyms: (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone
• CAS NO: 201856-48-6
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.28
• Mol File: 201856-48-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 399.225 °C at 760 mmHg
• Flash Point: 195.245 °C
• Appearance: /
• Density: 1.14
• CAS DataBase Reference: (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone(201856-48-6)
• EPA Substance Registry System: (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone(201856-48-6)

Safety Data

• Hazardous Substances Data: 201856-48-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure and chirality allow for the development of enantiomer-specific medications, which can have different therapeutic effects and reduce potential side effects.
Used in Drug Development:
(3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone is used as a starting material in drug development, enabling the creation of novel compounds with potential therapeutic applications. Its ability to inhibit certain enzymes and receptors makes it a valuable candidate for the treatment of various diseases and conditions.
Used in Medicinal Chemistry Research:
(3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone is used as a research tool in medicinal chemistry to study the structure-activity relationships of compounds and to optimize their pharmacological properties. Its unique features, such as the ethoxyethoxy and phenyl groups, provide insights into the design of more effective and selective drugs.
Used in Drug Synthesis:
(3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone is used in the synthesis of complex drug molecules, where its chiral centers and functional groups can be further modified to achieve the desired biological activity and pharmacokinetic properties. (3R,4S)-3-(1-Ethoxyethoxy)-4-phenyl-2-azetidinone serves as a versatile building block for the development of innovative therapeutic agents.

Upstream product

• 75-75-2 methanesulfonic acid 
• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 109-92-2 ethyl vinyl ether 
• 132127-31-2 3-Triisopropylsilyloxy-4-phenylazetidin-2-one 
• 100-52-7 benzaldehyde 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 132127-31-2 (3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one 

Downstream Products

• 201856-53-3 (3R,4S)-3-(1-ethoxyethoxy)-4-(phenyl)-N-benzoyl-2-azetidinone 
• 144629-55-0 2'-EE-10-Deacetyl-7,10-bis(trichloroethoxycarbonyl)-taxol 
• 114915-18-3 10-Deacetyl-7,10-bis(trichloroethoxycarbonyl)-taxol 
• 115437-19-9 2'-(1-Ethoxyethoxy)-7-triethylsilyltaxol 
• 33069-62-4 paclitaxel 
• 143843-07-6 7-(triethylsilyl)baccatin III 13-*)-1''-ethoxyethyl)-(2'R,3'S)-3'-phenylisoserinate> 
• 143842-96-0 baccatin III 13- 
• 143843-02-1 (3R,4S)-1-(p-chlorobenzoyl)-3-<((R^*)-1'-ethoxyethyl)oxy>-4-phenyl-2-azetidinone 
• 201856-57-7 1-tert-butoxycarbonyl-(3R,4S)-3-EEO-4-phenylazetidin-2-one 

Relevant articles and documents

A [...] he [...] synthesis process

A [...] he [...] synthesis process, in order to (3 R, 4 S) - 3 - hydroxy - 4 - phenyl - 2 - azetidinone as the starting material, adopts the one-pot synthesis, its first with vinyl ether condensation, with the BOC - anhydride is condensed directly [...] h

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

A highly efficient route to taxotere by the β-lactam synthon method

Taxotere, a highly promising anticancer drug, is synthesized through an efficient coupling of 7,10-diTroc-10-deacetylbaccatin III with enantiomerically pure (3R,4S)-1-tBOC-3-EEO- 4-phenylazetidin-2-one which is obtained via chiral ester enolate - imine cyclocondensation.

New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with excellent enantiomeric purity is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenyl-isoserine and its analogs. (3R,4S)-N-benzoyl-3-(1-ethoxyethoxy)-4-phenyl-2-azetidinone readily derived from the 3-hydroxy-4-phenyl-β-lactam is coupled with protected baccatin IIIs, followed by deprotection to give optically pure taxol and 10-deacetyl-7,10-bis(Troc)-taxol in good yields. Fully assigned 1H, 13C, and 2D (COSY and HETCOR) NMR spectra of taxol thus synthesized are shown and discussed.

Synthesis of biologically active taxol analogues with modified phenylisoserine side chains

Taxol (1) is a highly potent antitumor agent, exerting its mechanism of action by promoting the assembly of stable microtubules in cells. We are reporting on the first synthesis and biological evaluation of taxol derivatives with substituted phenyl rings

Method for preparation of taxol using an oxazinone

Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: STR1 wherein R1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R2 is hydrogen, ethoxyethyl, 2,2,2-tric