72888-48-3

Upstream product

• 86258-95-9 (3R,4S)-1-(di-p-anisylmethyl)-3-ethenyl-4-(l-menthyloxycarbonyl)-2-azetidinone 
• 137765-45-8 (3S,4S)-1-(di-p-anisylmethyl)-3-ethenyl-4-(d-menthyloxycarbonyl)-2-azetidinone 
• 1233825-17-6 (3R,4R)-4-acetoxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone 
• 86258-97-1 (3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone 
• 137765-47-0 (3R,4R)-4-acetoxy-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 86207-16-1 (3RS,4SR)-4-carboxy-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 86258-96-0 (3R,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 91603-19-9 (3R,4R)-4-acetoxy-1-(di-p-anisylmethyl)-3-<(R)-1-p-nitrobenzyloxycarbonyloxyethyl>-2-azetidinone 
• 86207-15-0 (3RS,4RS)-4-n-butoxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 96035-87-9 (2S,3R)-1-[Bis-(4-methoxy-phenyl)-methyl]-4-oxo-3-vinyl-azetidine-2-carbonyl chloride 

Downstream Products

• 80391-28-2 (3S,4R)-4-Allyl-3-[1-(R)-p-nitrobenzyloxycarbonyloxyethyl]-azetidin-2-one 

Relevant academic research and scientific papers

Synthetic studies of carbapenem and penem antibiotics. I. Facile synthesis of a key intermediate: 4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinone

A highly efficient synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, was accomplished. It was found that oxymercuration-reduction of easily obtainable 4-alkyloxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone could be employed as a key stereoselective reaction. The chiral starting material was obtained by optical resolution or asymmetric (2 + 2) cycloaddition. The desired product was afforded in four steps, that is, oxymercuration-reduction, oxidative decarboxylation, protection of the hydroxy group and removal of the N-protecting group.