733769-98-7

Upstream product

• 341554-34-5 methyl [(αR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] 
• 733769-99-8 (αR,2S,3R)-3-(1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid 
• 733769-96-5 (1R,2R,5S)-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptane-4,7-dione 
• 541-41-3 chloroformic acid ethyl ester 
• 733769-97-6 (1R,2R,4S,5S)-4-hydroxy-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptan-7-one 

Downstream Products

• 927678-30-6 (3R,4S)-3-[(1R)-1-(methanesulfonyloxy)ethyl]-4-[(methanesulfonyloxy)methyl]-1-(4-methoxyphenyl)azetidin-2-one 
• 927678-29-3 (1R,2R,5S)-6-(4-methoxyphenyl)-2-methyl-3-oxa-6-azabicyclo[3.2.0]heptan-7-one 

Relevant academic research and scientific papers

Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

All four trans-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (αR,6R,7R)- and (αS,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from l- and d-threonine, the configuration at the α-position was inverted by using Mitsunobu reactions providing the (αS,6R,7R)- and (αR,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out.

Synthesis of enantiomerically pure 2-isoxacephems

(αR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted β-lactams. The reduction of methyl [(αR,2S,3R)-3-(1-ace