67501-79-5

Upstream product

• 68485-45-0 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-azetidin-2-one 
• 68485-54-1 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(1-hydroxyethyl)azetidin-2-one 

Downstream Products

• 74660-90-5 benzyl (2RS,3RS,5SR,6RS,1'RS)-3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 74660-90-5 benzyl (2RS,3SR,5SR,6RS,1'RS)-3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate-chloroform hemisolvate 
• 74660-90-5 benzyl (2RS,3RS,5RS,6SR,1'SR)-3-(2-acetamidoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-80-8 (2RS,3SR,5RS,6SR,1'SR)-benzyl 3-chloro-6-(1-hydroxyethyl)-7-oxo-3-<(SR)-phenylsulfinyl>-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-81-9 (5RS,6SR,1'SR)-benzyl 6-(1-hydroxyethyl)-7-oxo-3-<(SR)-phenylsulfinyl>-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 
• 72669-81-9 (5RS,6SR,1'SR)-benzyl 6-(1-hydroxyethyl)-7-oxo-3-<(RS)-phenylsulfinyl>-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate*H2O 
• 72669-90-0 benzyl (2RS,3SR,5SR,6RS,1'RS)-6-(1-hydroxyethyl)-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-90-0 benzyl (2RS,3RS,5RS,6SR,1'SR)-6-(1-hydroxyethyl)-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-90-0 benzyl (2RS,3RS,5SR,6RS,1'RS)-6-(1-hydroxyethyl)-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 72669-90-0 (2R,5S,6R)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Olivanic Acid Analogues. Part 2. Total Synthesis of Some C(6)-Substituted 7-Oxo-1-azabicyclohept-2-ene-2-carboxylates

A number of 6-substituted 7-oxo-1-azabicyclohept-2-ene-2-carboxylates related to the olivanic acids were prepared from the phosphorane (32).Generation of the anion α to the azetidin-2-one carbonyl group, followed by reaction with electrophiles and intramolecular cyclisation using the Wittig procedure gave the bicyclic products; in all cases the thermodynamically favoured trans-stereochemisty about the azetidinone ring predominated.In contrast, some less readily available cis-substituted analogues were obtained from the cyclohexa-1,4-diene derived phosphorane (61).The synthetic utility of a masked acetonyl ester group for preparing the free acids of these azabicycloheptene ring systems is described.