76496-44-1

Usage

Class

Carboxylate compound

Structure

Bicyclic ring system

Functional Groups

Thioether group (ethylthio)
Hydroxyethyl group (1-hydroxyethyl)
Carbonyl group (oxo)
Allyl group

Chirality

(R*) configuration

Potential Applications

Pharmaceuticals
Biochemistry
Organic synthesis

Further Research

Required for precise uses and properties

Upstream product

• 74-96-4 ethyl bromide 
• 87131-55-3 (5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid allyl ester 
• 80629-48-7 (5R,6S)-3-Ethylsulfanyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 80629-49-8 (5S,6S)-3-Ethylsulfanyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 76431-41-9 (5R,6R)-3-Ethylsulfanyl-7-oxo-6-[(S)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 76431-37-3 allyl glyoxalate dihydrate 
• 76431-28-2 Carbonic acid 1-[1-(tert-butyl-dimethyl-silanyl)-2-ethylsulfanyl-4-oxo-azetidin-3-yl]-ethyl ester 2,2,2-trichloro-ethyl ester 
• 80629-64-7 Carbonic acid 1-[1-(tert-butyl-dimethyl-silanyl)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl]-ethyl ester 2,2,2-trichloro-ethyl ester 
• 76431-41-9 (5R,6R)-3-Ethylsulfanyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 76431-41-9 (5R,6S)-3-Ethylsulfanyl-7-oxo-6-[(S)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 80629-48-7 (5R,6S)-3-Ethylsulfanyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester 
• 76431-38-4 {(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-hydroxy-acetic acid allyl ester 
• 76431-30-6 Carbonic acid (S)-1-((2S,3R)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester 
• 76431-38-4 {(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(S)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-hydroxy-acetic acid allyl ester 

Downstream Products

• 77646-84-5 Sodium; (5R,6S)-3-ethylsulfanyl-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate 

Relevant academic research and scientific papers

Process for penem derivatives

An efficient process for converting readily available 4-acetoxy-2-azetidinones to allyl 2-thioxopenam-3-carboxylates, intermediates useful for the synthesis of penem antibiotics.

A NOVEL SYNTHESIS OF A 2-THIOXOPENAM

The synthesis of an optically active 2-thioxopenam through thermal rearrangement of a 2-t-butylsulfinylpenem to a penemsulfenic acid intermediate and its in situ deoxygenation is described.

SYNTHESIS OF RACEMIC, 2-(ALKYLTHIO)-6-(1-HYDROXYETHYL) PENEMS; ATTEMPTED PENEM SYNTHESIS VIA COPPER (I) - PROMOTED CYCLISATIONS

Stereocontrolled syntheses of the diastereoisomeric 6-(1-hydroxyethyl)-2-ethylthio and 2-(2-aminoethylthio)-penem-3-carboxylates from a common monocyclic azetidinone precursor are described.Cu (I)-promoted cyclisation of suitable N/C-3 secopenems is shown to yield "isopenems" (7-oxo-2-thia-1-azabicyclohept-3-enes) as the sole bicyclic product.

SYNTHESIS OF OPTICALLY ACTIVE PENEMS

A general synthesis for optically active penems is described.Penems undergo a novel thermal isomerisation reaction.