78184-67-5

Usage

Uses

Used in Pharmaceutical Industry:
(4-nitrophenyl)methyl [2S-[2alpha,5beta,6beta(S)]]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate is used as a pharmaceutical candidate for the development of new drugs due to its unique structure and functional groups. (4-nitrophenyl)methyl [2S-[2alpha,5beta,6beta(S)]]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate's potential applications may include the treatment of various diseases and conditions, given its ability to interact with biological targets and modulate biological pathways.
Used in Research and Development:
In the field of research and development, (4-nitrophenyl)methyl [2S-[2alpha,5beta,6beta(S)]]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate serves as a valuable compound for studying the effects of stereochemistry on biological activity. Its unique structure allows researchers to investigate the role of chiral centers in drug design and development, potentially leading to the discovery of more effective and selective therapeutic agents.
Used in Chemical Synthesis:
(4-nitrophenyl)methyl [2S-[2alpha,5beta,6beta(S)]]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate can be utilized as a key intermediate in the synthesis of other complex organic compounds. Its versatile structure and functional groups make it a suitable building block for the preparation of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Analytical Chemistry:
(4-nitrophenyl)methyl [2S-[2alpha,5beta,6beta(S)]]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate's unique structure and functional groups also make it a potential candidate for use in analytical chemistry. (4-nitrophenyl)methyl [2S-[2alpha,5beta,6beta(S)]]-6-(1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate can be employed as a chiral selector in chromatographic techniques, enabling the separation and analysis of enantiomers and other chiral compounds.

Upstream product

• 75321-07-2 4-[(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 78501-85-6 [(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 77120-91-3 (E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester 
• 74288-37-2 4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-butyric acid 4-nitro-benzyl ester 
• 77120-95-7 (2S,3R)-3-Amino-2-((S)-1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride 
• 77120-93-5 (2R,3R,4S)-4-Benzylamino-2-methyl-6-oxo-tetrahydro-pyran-3-carboxylic acid; hydrochloride 
• 77120-97-9 {(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acetic acid benzyl ester 
• 77120-94-6 t-4-amino-c-2-methyl-6-oxotetrahydropyran-r-3-carboxylic acid hydrochloride 
• 75321-07-2 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 75321-07-2 4-[(2S,3R)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 
• 77120-98-0 {(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acetic acid 
• 77120-96-8 benzyl -4-oxoazetidin-2-yl> acetate 
• 79543-87-6 4-[(2S,3R)-3-((S)-1-Formyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester 

Downstream Products

• 77396-88-4 (5R,6S)-3-(Diethoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 64067-13-6 (5R,6S)-6-(1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 64067-13-6 (5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 1497410-61-3 (2S,5R,6S)-4-nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-2-((phenylamino)methyl)-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1497410-62-4 (2S,5R,6S)-4-nitrobenzyl 6-((R)-1-hydroxyethyl)-2-((4-methoxyphenylamino)methyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1497410-63-5 (2S,5R,6S)-4-nitrobenzyl 2-((4-bromophenylamino)methyl)-6-((R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1497410-64-6 (2S,5R,6S)-4-nitrobenzyl 6-((R)-1-hydroxyethyl)-2-((S)-1-(4-methoxyphenyl)-2-nitroethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1497410-65-7 (2S,5R,6S)-4-nitrobenzyl 6-((R)-1-hydroxyethyl)-2-((R)-1-(4-methoxyphenyl)-2-nitroethyl)-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1497410-66-8 (2S,5R,6S)-4-nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-2-((R)-3-oxocyclopentyl)-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 1497410-67-9 (2S,5R,6S)-4-nitrobenzyl 6-((R)-1-hydroxyethyl)-3,7-dioxo-2-((S)-3-oxocyclopentyl)-1-azabicyclo[3.2.0]heptane-2-carboxylate 

Relevant academic research and scientific papers

METHOD OF PREPARING INTERMEDIATES OF PENEM ANTIBIOTICS

The present invention relates to a method of preparing bicyclic keto esters, which are intermediates for carbapenem-based antibiotics. The method of preparing carbapenem-based antibiotic intermediates according to the present invention has not only the fast reaction rate using co-catalysts and specific reaction solvents which may be allowed to have high activity of rhodium catalysts, but also reduces the amount of expensive rhodium catalysts. Therefore, the present invention is very economical and useful, in industrial aspects.

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.

A PRACTICAL SYNTHESIS OF (+/-)-THIENAMYCIN

An efficient and operationally simply synthesis of (+/-)-thienamycin is described.