80353-26-0

Basic information

• Product Name: 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)-
• Synonyms: 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)-;(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;(2S,5R,6S)-Benzhydryl 6-broMo-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide;(2S,5R,6S)-6-BROMO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID DIPHENYLMETHYL ESTER, 4-OXIDE;(2S,5R,6S)-Benzhydryl 6-bromo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxyla
• CAS NO: 80353-26-0
• Molecular Formula: C₂₁H₂₀BrNO₄S
• Molecular Weight: 462.3568
• Mol File: 80353-26-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 629.066°C at 760 mmHg
• Flash Point: 334.247°C
• Appearance: /
• Density: 1.582g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: 2-8°C
• PKA: -6.06±0.70(Predicted)
• CAS DataBase Reference: 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)-(CAS DataBase Reference)
• NIST Chemistry Reference: 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)-(80353-26-0)
• EPA Substance Registry System: 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)-(80353-26-0)

Safety Data

• Hazardous Substances Data: 80353-26-0(Hazardous Substances Data)

Usage

General Description

The chemical "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 a complex compound with a bicyclic structure and a carboxylic acid functional group. It contains a bromo group and a diphenylmethyl ester, as well as a 4-oxide substituent. The compound is classified as a 4-oxo-piperidine derivative and is chiral, with the stereochemistry described as (2S,5R,6S). Due to its intricate structure and functional groups, this compound likely has a range of potential chemical and biological applications.

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

• 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 
• 74189-25-6 diphenylmethyl 6α-bromopenicillanate 
• 551-16-6 6-aminopenicillanic acid 
• 205320-26-9 6α-Bromopenicillanic acid 

Downstream Products

• 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 
• 89786-04-9 tazobactam acid 
• 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 
• 85573-72-4 (R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester 
• 89051-48-9 Benzhydryl 2β-bromomethyl-2α-methyl-6,6-dihydropenicillanate 
• 85573-73-5 2β-chloromethyl-2α-methylpenicillin-3α-carboxylic acid diphenylmethyl ester 
• 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 
• 89786-04-9 tazobactam 
• 122661-93-2 2α-methyl-2β-[(1,2,3-triazol-1-yl)methyl]penicillin-3α-carboxylic acid diphenylmethyl ester 

Relevant articles and documents

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.

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

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.