137440-00-7

Upstream product

• 137439-98-6 p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 112563-66-3 Benzoic acid (1S,5R,6S)-7-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-8-oxo-7-aza-bicyclo[4.2.0]oct-3-en-5-yl ester 
• 137439-97-5 p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 112563-67-4 p-Nitrobenzyl (4RS,5SR,6SR)-4-benzoyloxy-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 
• 137439-99-7 p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-chloro-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate 

Relevant academic research and scientific papers

Olivanic Acid Analogues. Part 9. Allylic Oxidative Functionalisation of Substituted Azetidinones: Synthesis of Some 4-Acyloxy-7-oxo-1-azabicyclohept-2-ene-2-carboxylates

Sharpless oxidation (ButO2H), SeO2) of the protected allyl azetidinone 7 gave the allylic alcohol 8 which was transformed to the 5,6-trans-4α-acetoxyolivanic acid derivative 16.Kharasch-Sosnovsky benzoyloxylation (PhCO3But, CuCl, PhH, heat) of the silylated 7-azabicyclooct-3-enes 17b,c provided inter alia allylic benzoates 18b,c and 21b,c.These were synthetic precursors of the 5,6-cis-olivanic acid analogues 23 and 26, which contain 8- and 4α-benzoyloxy groups, respectively.