86258-97-1

Upstream product

• 86207-15-0 (3RS,4RS)-4-n-butoxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 86207-14-9 [(E)-Bis-(4-methoxy-phenyl)-methylimino]-acetic acid butyl ester 
• 86207-16-1 (3RS,4SR)-4-carboxy-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 91538-21-5 (3S,4S)-3-acetyl-1-(di-p-anisylmethyl)-4-(l-menthyloxycarbonyl)-2-azetidinone 
• 91538-20-4 [(E)-Bis-(4-methoxy-phenyl)-methylimino]-acetic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 91538-22-6 (3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4--2-azetidinone 
• 86258-96-0 (3R,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 19293-62-0 p,p'-dimethoxybenzhydrylamine 
• 91538-19-1 (3SR,4SR)-4-benzyloxycarbonyl-1-(di-p-anisylmethyl)-3-<(RS)-1-hydroxyethyl>-2-azetidinone 
• 86207-21-8 (3SR,4SR)-4-carboxy-1-(di-p-anisylmethyl)-3-<(RS)-1-hydroxyethyl>-2-azetidinone 
• 91538-18-0 3-acetyl-1-(di-p-anisylmethyl)-4-benzyloxycarbonyl-2-azetidinone 
• 91538-19-1 (3SR,4SR)-4-benzyloxycarbonyl-1-(di-p-anisylmethyl)-3-<(SR)-1-hydroxyethyl>-2-azetidinone 
• 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 

Downstream Products

• 104362-85-8 (3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4-methoxycarbonyl-2-azetidinone 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 143139-22-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-methylethenyl)-2-azetidinone 
• 104362-57-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-hydroxymethylethenyl)-2-azetidinone 
• 104362-56-3 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-chloromethylethenyl)-2-azetidinone 
• 104362-99-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone 
• 104362-86-9 (3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4-(1-hydroxy-1-methylethyl)-2-azetidinone 
• 112057-69-9 Carbonic acid benzyl ester (R)-1-{(2R,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 105557-93-5 Carbonic acid benzyl ester (R)-1-{(2R,3S)-2-[1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 143139-23-5 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone 
• 104362-83-6 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<1-(2-tetrahydropyranyloxy)methylethenyl>-2-azetidinone 
• 104362-59-6 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-tert-butyldimethylsilyl-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone 
• 104362-92-7 Carbonic acid benzyl ester (R)-1-[(2R,3S)-2-[1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-oxo-1-(tetrahydro-pyran-2-yl)-azetidin-3-yl]-ethyl ester 
• 104362-82-5 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(2-tetrahydropyranyl)-4-<1-(2-tetrahydropyranyloxy)methylethenyl>-2-azetidinone 

Relevant academic research and scientific papers

Synthetic studies of carbapenem and penem antibiotics. II. Synthesis of 3-acetyl-2-azetidinones by (2 + 2) cycloaddition of diketene and schiff bases

It was found that (2 + 2) cycloaddition reaction of diketene with Schiff bases was effectively promoted by imidazole as a catalyst to afford 3-acetyl-2-azetidinone derivatives 4. As an application of this new method, a practical asymmetric synthesis of 4 and its conversion into (3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-[(R)-1-hydroxyethyl]-2-azeti dinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, were accomplished.

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.