87542-16-3

Upstream product

• 85621-92-7 ethyl 1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidinecarboxylate 
• 85621-92-7 trans ethyl 1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidinecarboxylate 
• 85621-92-7 Ethyl (2RS,3SR)-1-(2,4-Dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidine-2-carboxylate 
• 115855-61-3 (2S,3S)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidine-2-carboxylic acid benzhydryl ester 
• 81902-49-0 diethyl N-(2,4-dimethoxybenzyl)-amino-malonate 
• 96724-73-1 N-benzyl-1-(2,4-dimethoxyphenyl)methanamine 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 115855-61-3 (2R,3S)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidine-2-carboxylic acid benzhydryl ester 
• 87542-16-3 1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidine-2-carboxylic acid 
• 83304-60-3 benzyl (2,4-dimethoxybenzyl)-amine 
• 85621-94-9 Diethyl-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolane-2-yl)-4-oxo-2,2-azetidine-dicarboxylate 
• 83304-64-7 diethyl 3-acetyl-1-(2,4-dimethoxybenzyl)-4-oxo-2,2-azetidine-dicarboxylate 
• 83304-63-6 1-(2,4-Dimethoxy-benzyl)-3-hydroxy-3-methyl-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 83304-61-4 diethyl(N-benzyl)-N-(2,4-dimethoxy-benzyl)-amino-malonate 

Downstream Products

• 81902-54-7 (2S,3S)-1-(2,4-Dimethoxy-benzyl)-3-(1-hydroxy-ethyl)-4-oxo-azetidine-2-carboxylic acid 
• 108908-23-2 diethyl (RS,3SR)-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidin-2-ylmalonate 
• 115855-63-5 (2R,3R)-3-(2-Methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidine-2-carboxylic acid benzhydryl ester 
• 115855-61-3 (2S,3S)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidine-2-carboxylic acid benzhydryl ester 
• 115855-61-3 (2R,3S)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidine-2-carboxylic acid benzhydryl ester 
• 87542-16-3 (2RS,3SR)-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidine-2-carboxylic acid 
• 87542-18-5 [(2S,3R)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidin-2-yl]-acetic acid 
• 87906-18-1 p-nitrobenzyl4-<(2RS,3RS)-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidin-2-yl>-3-oxobutanoate 
• 87542-19-6 [(2S,3R)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidin-2-yl]-acetic acid benzhydryl ester 
• 87542-45-8 p-nitrobenzyl (5RS,6SR)-2-(2-formylaminoethylthio)-6-(2-methyl-1,3-dioxolan-2-yl)carbapen-2-em-3-carboxylate 
• 87542-40-3 4-[(2R,3S)-1-(2,4-Dimethoxy-benzyl)-3-(2-methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid ethyl ester 
• 87542-46-9 p-nitrobenzyl (3RS,5RS,6SR)-6-(2-methyl-1,3-dioxolan-2-yl)-2-oxocarbapenam-3-carboxylate 
• 87542-47-0 4-[(2S,3R)-3-(2-Methyl-[1,3]dioxolan-2-yl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 87542-44-7 (5S,6R)-3-Benzylsulfanyl-6-(2-methyl-[1,3]dioxolan-2-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Simple and Condensed β-Lactams. Part 9. Elaboration of the 3-(1-Hydroxyethyl) Side Chains of Potential Intermediates of Carbapenem Antibiotics via the 2-Methyl-1,3-dioxolan-2-yl Group

Deketalization of the trans compounds methyl and ethyl (2RS,3RS)-1-(2,4-dimethoxybenzyl)-3-(2-methyl-1,3-dioxolan-2-yl)-4-oxoazetidine-2-carboxylates 5b and 5c, and of the cis isomer (6b) of the latter leads to 85:15 mixtures of the trans- and cis-compounds methyl (2RS,3RS)- and (2RS,3SR)-3-acetyl-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate (7a) and (8a), respectively of the corresponding ethyl esters (7b) and (8b).Sodium borohydride reduction of the mixture of the trans- and cis-esters (7b) and (8b) gives a mixture of the 1'-epimeric trans-compounds ethyl(2RS,3RS)-1-(2,4-dimethoxybenzyl)-3--4-oxazetidine-2-carboxylate (9b) and (10b).Similar mixtures of 1'-epimeric compounds of the types (9) and (10), carrying a variety of substituents attached to position 2 of their azetidine rings were obtained by successive deketalization and reduction of the corresponding trans-(5) and cis-(6) compounds or their mixtures, as well as by other methods.Ring closure of a mixture of the pair of the 1'-epimeric trans-compounds p-nitrobenzyl 2-diazo-4--4-oxo-azetidin-2-yl>-3-oxobutanoates (9n) and (10n) gave a mixture of the 1'-epimeric compounds p-nitrobenzyl 6--2,7-dioxo-(3RS,5RS,6SR)-carbapenam-3-carboxylates (11) and (12) which was converted into a mixture (13) of the 1'-epimeric bis-protected thienamycin analogues p-nitrobenzyl 2-(2-formylaminoethylthio)-6--7-oxo-(5RS,6SR)-carbapen-2-em-3-carboxylates.

SIMPLE AND CONDENSED β-LACTAMS-I. THE APPLICATION OF DIKETENE IN β-LACTAM SYNTHESIS. THE SYNTHESIS AND FUNCTIONAL GROUP MANIPULATIONS OF DIETHYL 3-ACETYL-4-OXOAZETIDINE-2,2-DICARBOXYLATES

Acetylation of the N-substituted diethyl aminomalonates 3a-3d with diketene furnished the ring tautomers 6a-6d of the expected acetoacetyl derivatives 5.By treatment with iodine and sodium ethoxide compounds 6a-6d are smoothly converted into the β-lactam