68485-41-6

Upstream product

• 7723-14-0 phosphorane 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 68485-39-2 benzyl (8-oxo-7-azabicyclo<4.2.0>oct-3-en-7-yl)-1-hydroxyacetate 
• 68485-40-5 benzyl 8-oxo-7-azabicyclo<4.2.0>oct-3-en-7-yl(triphenylphosphoranylidene)acetate 
• 104883-17-2 Chloro-(8-oxo-7-aza-bicyclo[4.2.0]oct-3-en-7-yl)-acetic acid benzyl ester 
• 20205-48-5 8-oxo-7-azabicyclo<4.2.0>oct-2-ene 
• 52709-42-9 benzylglyoxylate 
• 68693-10-7 benzyl (5RS,6SR)-6-(2-oxoethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 

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.

Bicyclic β-lactam antibiotics

Compounds of the formula (I): STR1 wherein G is hydrogen, alkyl, alkenyl, substituted alkyl or substituted alkenyl, R1 is alkyl or aryl, substituted alkyl or substituted aryl, and R is an organic group such that --CO2 R is an ester group are produced. The compounds are useful as antibacterial and β-lactamase inhibitory agents.