80353-26-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-bromo-3,3-dimethyl-7-oxo-, diphenylmethyl ester, 4-oxide, (2S,5R,6S)is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure and functional groups enable it to serve as a building block for the development of novel therapeutic agents with potential applications in treating various diseases.
Used in Chemical Synthesis:
In the chemical synthesis industry, 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-bromo-3,3-dimethyl-7-oxo-, diphenylmethyl ester, 4-oxide, (2S,5R,6S)is used as a key intermediate in the preparation of complex organic molecules. Its versatile functional groups allow for further chemical modifications, making it a valuable component in the synthesis of advanced materials and specialty chemicals.
Used in Research and Development:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-bromo-3,3-dimethyl-7-oxo-, diphenylmethyl ester, 4-oxide, (2S,5R,6S)is utilized in research and development for studying its chemical properties, reactivity, and potential applications. Its unique structure and chirality make it an interesting subject for exploring new reaction pathways and developing innovative synthetic methods.
Used in Chiral Compounds Synthesis:
In the field of chiral compounds synthesis, 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-bromo-3,3-dimethyl-7-oxo-, diphenylmethyl ester, 4-oxide, (2S,5R,6S)is employed as a chiral building block. Its defined stereochemistry allows for the preparation of enantiomerically pure compounds, which are essential in various applications, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C21H20BrNO4S/c1-21(2)17(23-18(24)15(22)19(23)28(21)26)20(25)27-16(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12,15-17,19H,1-2H3/t15-,17-,19+,28?/m0/s1

Upstream product

• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 79703-02-9 6α-bromopenicillan-3α-carboxylic acid-1β-oxide 
• 908093-98-1 diazodiphenylmethane 
• 24138-28-1 6-bromopenicillanic acid 
• 5350-57-2 benzophenone hydrazone 
• 551-16-6 6-Aminopenicillanic Acid 
• 551-16-6 6-aminopenicillanic acid 
• 205320-26-9 6α-Bromopenicillanic acid 

Downstream Products

• 87579-78-0 diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 
• 99651-36-2 benzhydryl 6α-bromopenicillanate S,S-dioxide 
• 188249-92-5 diphenylmethyl (2S,3R,5R)-3-formyl-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate 
• 182750-65-8 benzhydryl 2β-hydroxymethyl-1,1-dioxopenicillanate 
• 182750-66-9 (2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester 
• 87579-79-1 (R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate 
• 89789-07-1 (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester 
• 89786-04-9 tazobactam acid 
• 229309-36-8 (2S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229309-35-7 (2S,5R,6S)-6-((S)-1-Hydroxy-ethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 229309-34-6 (2S,5R,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester 
• 205320-23-6 benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide 
• 89786-04-9 tazobactam 
• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 

Relevant academic research and scientific papers

Application of Continuous Flow in Tazobactam Synthesis

Tazobactam is a β-lactamase inhibitor. In this work, a combination of continuous flow and batch experiments for the synthesis of tazobactam has been developed. The first three steps and the preparation of the peroxyacetic acid are continuously carried out in the microreactors, which improves the procedure safety and efficiency. There is also a final step of the deprotection reaction in the microreactor, which can increase the yield and reduce the formation of impurities. Under optimized process conditions, the total yield of the target product reached 37.09% (30.93% in batch). The continuous flow method not only greatly reduces the reaction time but also significantly improves procedure safety and increases the yield.

Preparation method of 6alpha-bromopenicillanic-3alpha- carboxylic di-methylphenyl-1beta-oxide

The invention discloses a preparation method of 6alpha-bromopenicillanic-3alpha-carboxylic di-methylphenyl-1beta-oxide. According to the method, acetone is used as a catalyst; benzophenone hydrazone takes an oxidation reaction with KMnO4 under the acid condition to generate diazodiphenylmethane reaction liquid; then, the reaction liquid is dripped into the 6alpha-bromopenicillanic-3alpha-carboxylic di-methylphenyl-1beta-oxide to obtain a product. The method has the advantages that the method is simple; the use is safe; the environment-friendly effect is achieved; the product purity is high; the yield is high, and the like. The reaction equation is shown as the accompanying drawing.

Crystal structures of KPC-2 β-lactamase in complex with 3-nitrophenyl boronic acid and the penam sulfone PSR-3-226

Class A carbapenemases are a major threat to the potency of carbapenem antibiotics. A widespread carbapenemase, KPC-2, is not easily inhibited by β-lactamase inhibitors (i.e., clavulanic acid, sulbactam, and tazobactam). To explore different mechanisms of inhibition of KPC-2, we determined the crystal structures of KPC-2 with two β-lactamase inhibitors that follow different inactivation pathways and kinetics. The first complex is that of a small boronic acid compound, 3-nitrophenyl boronic acid (3-NPBA), bound to KPC-2 with 1.62-A resolution. 3-NPBA demonstrated a Km value of 1.0±0.1 μM (mean±standard error) for KPC-2 and blocks the active site by making a reversible covalent interaction with the catalytic S70 residue. The two boron hydroxyl atoms of 3-NPBA are positioned in the oxyanion hole and the deacylation water pocket, respectively. In addition, the aromatic ring of 3-NPBA provides an edge-to-face interaction with W105 in the active site. The structure of KPC-2 with the penam sulfone PSR-3-226 was determined at 1.26-A resolution. PSR-3-226 displayed a Km value of 3.8±0.4 μM for KPC-2, and the inactivation rate constant (k inact) was 0.034±0.003 s-1. When covalently bound to S70, PSR-3-226 forms a trans-enamine intermediate in the KPC-2 active site. The predominant active site interactions are generated via the carbonyl oxygen, which resides in the oxyanion hole, and the carboxyl moiety of PSR-3-226, which interacts with N132, N170, and E166. 3-NPBA and PSR-3-226 are the first β-lactamase inhibitors to be trapped as an acyl-enzyme complex with KPC-2. The structural and inhibitory insights gained here could aid in the design of potent KPC-2 inhibitors. Copyright

A new approach to the synthesis of tazobactam using an organosilver compound

Tazobactam (9) was synthesized in 8 steps from the readily accessible 6-APA. By the first use of silver triazole as reactant, the formation of the isomer 7 was avoided and a total yield of 50%, which was two to three times higher than that of reported procedures for 9, was obtained. Georg Thieme Verlag Stuttgart.

STEREOSELECTIVE SYNTHESIS OF 6α-HALOPENICILLANATES BY SAMARIUM(II) IODIDE PROMOTED REDUCTION OF 6,6-DIHALOPENICILLANATES

A mild an efficient samarium(II) iodide promoted-reduction of 6,6-dibromopenicillanates for stereoselective synthesis of 6α-bromopenicillanates has been developed.