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

General Description

The chemical "(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 compound with a cyclohexane ring and an azetidin-2-one moiety. It contains a substituent on the 3rd carbon atom that is a (R)-1-tert-butyldimethylsilyloxy-ethyl group and a substituent on the 4th carbon atom that is a (2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl group. The compound has a stereochemistry of (3S,4R) and is commonly used in organic synthesis and medicinal chemistry research.

Upstream product

• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 155320-76-6 (2S)-2-methoxycyclohexanone 
• 87037-95-4 (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one 
• 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 
• 184531-13-3 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one 
• 184531-15-5 (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yloxy)-cyclohex-2-enyl]-azetidin-2-one 
• 1655-06-7 cis-ethyl 2-hydroxy-cyclohexanoate 

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 
• 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 
• 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 

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