4052-54-4

Basic information

• Product Name: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide
• Synonyms: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide;Benzylpenicillinsulfoxide;penicillin G sulfoxide;(6R)-6-(Phenylacetylamino)penicillanic acid 4-oxide;Penicillin G sulphoxide;(2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-(2-phenylethanoylamino)-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R,6R)-4,7-diketo-3,3-dimethyl-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS NO: 4052-54-4
• Molecular Formula: C₁₆H₁₈N₂O₅S
• Molecular Weight: 350.38952
• EINECS: 223-757-0
• Mol File: 4052-54-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 762.8°Cat760mmHg
• Flash Point: 415.1°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 1.84E-24mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide(4052-54-4)
• EPA Substance Registry System: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide(4052-54-4)

Safety Data

• Hazardous Substances Data: 4052-54-4(Hazardous Substances Data)

Usage

Description

[2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide is a complex chemical compound belonging to the penicillin class of antibiotics. It features a 4-thia-1-azabicyclo[3.2.0]heptane ring and a phenylacetamido side chain, with 3,3-dimethyl and 7-oxo groups that contribute to its stability and biological activity. This β-lactam antibiotic works by inhibiting bacterial cell wall synthesis, making it a potential therapeutic agent for treating bacterial infections.

Uses

Used in Pharmaceutical Industry:
[2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide is used as an antibiotic for the treatment of various bacterial infections. Its ability to interfere with bacterial cell wall synthesis makes it a valuable compound in combating resistant strains of bacteria and providing effective treatment options for patients.
Used in Research and Development:
In the field of medical research, this compound serves as a valuable tool for studying the mechanisms of bacterial resistance to antibiotics and the development of new drugs to combat antibiotic-resistant infections. Its unique structure and properties can be further explored to design more effective and targeted antibiotics with fewer side effects.
Used in Drug Delivery Systems:
Similar to other antibiotics, [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide can be incorporated into drug delivery systems to improve its bioavailability, targeting, and overall therapeutic efficacy. This may involve the use of nanoparticles, liposomes, or other advanced drug delivery technologies to enhance the compound's performance in treating bacterial infections.

InChI:InChI=1/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24(16)23)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-,24?/m1/s1

Upstream product

• 113-98-4 Penicillin G potassium 
• 61-33-6 penicillin G 
• 1254-56-4 benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 39906-59-7 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid; potassium salt 
• 653-89-4 penicillin G methyl ester 
• 51446-87-8 diphenylmethyl 6β-(2-phenylacetamido)penicillanate 1-oxide 
• 99673-35-5 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid cyanomethyl ester 
• 4052-68-0 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid benzyl ester 
• 40578-79-8 1ξ-oxo-6β-(2-phenyl-acetylamino)-1λ⁴-penicillanic acid methyl ester 

Downstream Products

• 121894-91-5 (2S,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid phenylacetoxymethyl ester 
• 121894-92-6 (R)-3-Methyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid phenylacetoxymethyl ester 
• 121894-93-7 (R)-3-Methoxy-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid phenylacetoxymethyl ester 
• 27255-72-7 7-phenylacetamidodesacetoxycephalosporanic acid 
• 130164-50-0 (R)-2-{(2R,3R)-2-[(2R,3R)-1-((R)-1-Benzhydryloxycarbonyl-2-methyl-propyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-butyric acid benzhydryl ester 
• 130164-51-1 (R)-2-{(2R,3R)-2-[(2R,3R)-1-((R)-1-Carboxy-2-methyl-propyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-3-methyl-butyric acid 
• 130164-49-7 (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-butyric acid benzhydryl ester 
• 119944-09-1 (R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzhydryl ester 
• 79386-26-8 methyl 2-<(3S)-4-(benzothiazol-2-ylthio)-2-oxo-3-phenylacetamidoazetidin-1-yl>-3-methylbut-2-enoate 
• 79434-35-8 methyl (2R)-2-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-3-enoate 
• 79386-27-9 (1S,5R)-3-phenylmethyl-6-<(1R)-1-carboxy-2-methylprop-2-enyl>-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-7-one 
• 79386-29-1 1-dethia-1-oxa-5-epi-anhydropenicillin 
• 79386-28-0 (2R,5S,6S)-2-(1-methylethenyl)-6-phenylacetamido-4-oxa-1-azabicyclo<3.2.0>heptane-3,7-dione 
• 34104-19-3 methyl 2-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-methylbut-2-enoate 

Relevant articles and documents

Study on crystal morphology of penicillin sulfoxide in different solvents using binding energy

The binding energy of the solvent is an important factor in crystal morphology. In this study, binding energies of water, ethyl acetate, and butyl acetate on specific surfaces of penicillin sulfoxide were evaluated. Molecular modeling techniques based on the adsorption of solvent molecules on specific crystal surfaces were utilized to determine the binding energies. Our results show a strong association between the absolute value of the binding energy and crystallization. The results predicted by molecular modeling are well-fitted with experimental results. Efficient solvent selection and production process optimization were successfully achieved by using the methodology developed in this paper. Our study illustrates a novel strategy that can be used for the investigation of solvent effects.

Industrial production method for preparing penicillin sulfoxide by continuously oxidizing penicillin

The invention discloses an industrial production method for preparing penicillin sulfoxide by continuously oxidizing penicillin, and belongs to the field of pharmaceutical chemicals; a continuous reaction method is adopted, a penicillin solution and peracetic acid or other oxidants simultaneously flow into a mixer or a microreactor according to a certain proportion, and a penicillin sulfoxide solution is obtained by reaction at high temperature and in short time; the method can be used for an oxidation process of a process for preparing penicillin sulfoxide by taking penicillin fermentation liquor, filtrate, BA, RB, penicillin industrial salt and the like as initial raw materials, and solves the problem that the reaction temperature and the reaction time are influenced by mass transfer and low heat transfer efficiency of batch reaction; therefore, the problems of poor reaction liquid quality and low reaction yield are solved, and the yield of penicillin sulfoxide is high.

Deprotection of carboxylic esters of β-lactam homologues. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix

-