135297-22-2

Basic information

• Product Name: (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one
• Synonyms: (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one
• CAS NO: 135297-22-2
• Molecular Weight: 355.55
• Mol File: 135297-22-2.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one(135297-22-2)
• EPA Substance Registry System: (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one(135297-22-2)

Safety Data

• Hazardous Substances Data: 135297-22-2(Hazardous Substances Data)

Usage

Description

(3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one is a complex organic compound characterized by its cyclohexane ring and azetidin-2-one moiety. It features a stereochemistry of (3S,4R) and includes a (R)-1-tert-butyldimethylsilyloxy-ethyl group on the 3rd carbon atom and a (2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl group on the 4th carbon atom. (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one is widely utilized in the fields of organic synthesis and medicinal chemistry research due to its unique structural properties and potential for various applications.

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

• 87037-95-4 (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one 
• 155320-76-6 (2S)-2-methoxycyclohexanone 
• 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 
• 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 
• 188396-09-0 3-Methoxy-2-oxo-cyclohexanecarboxylic acid allyl ester 
• 7429-44-9 2-methoxycyclohexanone 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-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 
• 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 
• 66057-15-6 (6-methoxy-cyclohex-1-enyloxy)-trimethyl-silane 
• 86978-81-6 (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone 
• 67-56-1 methanol 
• 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 
• 135297-04-0 (3S,4R)-4-[(1R,2S,3R)-2,3-epoxycyclohexyl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-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 articles and documents

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.

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.

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