135297-22-2

Usage

Uses

Used in Organic Synthesis:
(3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one is used as a key intermediate in organic synthesis for the development of novel chemical entities. Its unique structural features allow for the creation of a diverse range of compounds with potential applications in various industries.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one serves as a valuable building block for the design and synthesis of new pharmaceutical compounds. Its structural complexity and versatility make it an attractive candidate for the development of innovative drugs with improved efficacy and selectivity.
Used in Pharmaceutical Development:
(3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one is employed as a starting material in the pharmaceutical industry for the synthesis of new drugs. Its unique structural elements can be exploited to create molecules with enhanced pharmacological properties, potentially leading to the development of more effective treatments for various diseases.
Used in Chemical Research and Development:
This complex compound is also utilized in chemical research and development, where it can be used to explore new reaction pathways, study the effects of structural modifications on chemical and physical properties, and develop new methodologies for the synthesis of complex organic molecules.

Upstream product

• 67-56-1 methanol 
• 135297-04-0 (3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 
• 184531-17-7 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1R,2R,6R)-1-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-azetidin-2-one 
• 66057-15-6 (6-methoxy-cyclohex-1-enyloxy)-trimethyl-silane 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 7429-44-9 2-methoxycyclohexanone 
• 86978-81-6 (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone 
• 135297-20-0 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-3-methoxy-2-oxo-cyclohex-3-enyl)-azetidin-2-one 
• 181798-21-0 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3S)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one 
• 155320-76-6 (2S)-2-methoxycyclohexanone 
• 188396-09-0 3-Methoxy-2-oxo-cyclohexanecarboxylic acid allyl ester 
• 188396-10-3 1-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-methoxy-2-oxo-cyclohexanecarboxylic acid allyl ester 
• 188396-11-4 1-{(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-methoxy-2-oxo-cyclohexanecarboxylic acid allyl ester 
• 23740-37-6 2-methoxycyclohex-2-en-1-one 

Downstream Products

• 181798-22-1 [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((1R,3S)-3-methoxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-oxo-acetic acid benzyl ester 
• 135446-51-4 (1S,5S,8aS,8bR)-1-((R)-1-Hydroxy-ethyl)-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester 
• 181798-23-2 (1S,5S,8aS,8bR)-1-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methoxy-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

The use of zinc enolates in the synthesis of a key intermediate for the preparation of trinem antibiotics

The stereoselective preparation of 2a, a key intermediate in the synthesis of the broad spectrum tricyclic β-lactam antibiotic GV104326 1, by the reaction of a zinc enolate derived from chiral non-racemic 2-methoxycyclohexanone with azetidinone 3 is described.

Stereoselective synthesis of a key intermediate of sanfetrinem by means of a chelated tin(IV) enolate

(2S)-2-Methoxycyclohexanone [(2S)-6], reacts with the 4-acetoxyazetidinone 3a in the presence of SnCl4 and a tertiary amine base (such as N,N-diisopropylethylamine) to give the ketoazetidinone 5 (a key intermediate in the synthesis of the broad

Alkyl groups on the metal enhance the reactivity of the 'classical' zirconium enolate of 1-methoxycyclohexanone

Compound 2 is the key intermediate in the preparation of our lead trinem antibiotic sanfetrinem 1a. In this communication it is described how a modified 'Evans' zirconium enolate of 1-methoxycyclohexanone is able to react with acetidinone 3 in the presence of LiHMDS under strict kinetic conditions, giving 2 with good yield and selectivity. Copyright (C) Elsevier Science Ltd.

4-Substituted trinems as broad spectrum β-lactamase inhibitors: Structure-based design, synthesis, and biological activity

A wide variety of pathogens have acquired antimicrobial resistance as an inevitable evolutionary response to the extensive use of antibacterial agents. In particular, one of the most widely used antibiotic structural classes is the β-lactams, in which the

Process for producing cyclohexylazetidinone

A process for producing cyclohexylazetidinone expressed by the formula(IV) comprises condensing the magnesium enolate compound expressed by the formula (II) with acyloxyazetidinone expressed by the formula (III), wherein Me is a methyl group; R1/sup

Highly stereocontrolled synthesis of enantiomeric 4-methoxy trinems via resolution of scalemic enol phosphates

Stereocontrolled syntheses of 4-methoxy trinem 2 and its enantiomer 3 were achieved using the ester enolate N-trimethylsilylimine approach. The key step was the resolution of racemic enolphosphates derived from ephedrine.

The stereoselective synthesis of a key intermediate of the trinem antibiotic Sanfetrinem

By modulating the reactivity of the Lewis acid promoter it was possible to obtain, in a single stereoselective condensation step, the methoxyketone 7, an advanced intermediate in the synthesis of Sanfetrinem GV 104326.

Synthesis and antibacterial activity of 4- and 8-methoxy trinems

The synthesis of all the isomers of 8-methoxy-(9S,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.20. 03,8]-undec-2-ene-carboxylates 2 and 4-methoxy-(9R,10S,12R)-10-(1-hydroxyethyl)-11-oxo-1-azatricyclo-[7.2.0 .03,8]-undec-2-ene

A highly stereoselective and practical total synthesis of the tricyclic β-lactam antibiotic GV104326 (4-methoxytrinem)

A novel and practical total synthesis of a tricyclic β-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the high

The synthesis of a key intermediate of tricyclic betalactam antibiotics

By employing an intramolecular Sakurai-type olefination it was possible to obtain the olefin 5, a key intermediate in the synthesis of the broad spectrum tricyclic β-lactam antibiotic GG-326 1.