4888-90-8

Basic information

• Product Name: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide
• Synonyms: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide;penicillin V sulfoxide;(2S,5S,6R)-3,3-Dimethyl-7-oxo-6α-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid-4-oxide;(2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[[2-(phenoxy)acetyl]amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R,6R)-3,3-dimethyl-4,7-dioxo-6-[2-(phenoxy)ethanoylamino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,5R,6R)-4,7-diketo-3,3-dimethyl-6-[[2-(phenoxy)acetyl]amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS NO: 4888-90-8
• Molecular Formula: C₁₆H₁₈N₂O₆S
• Molecular Weight: 366.38892
• EINECS: 225-507-6
• Mol File: 4888-90-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 167-168 °C (decomp)
• Boiling Point: 780.2°Cat760mmHg
• Flash Point: 425.6°C
• Appearance: /
• Density: 1.54g/cm³
• PKA: 2.61±0.60(Predicted)
• CAS DataBase Reference: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-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-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide(4888-90-8)
• EPA Substance Registry System: [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide(4888-90-8)

Safety Data

• Hazardous Substances Data: 4888-90-8(Hazardous Substances Data)

Usage

Description

[2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide is a complex bicyclic compound with a carboxylic acid group, phenoxyacetamido group, and a thioether group. It is a derivative of a beta-lactam antibiotic, characterized by its potential reactivity and oxidizing properties due to the presence of oxo and oxide functional groups. [2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide is likely to have antimicrobial and pharmaceutical applications, primarily for the treatment of bacterial infections.

Uses

Used in Pharmaceutical Industry:
[2S-(2alpha,5alpha,6beta)]-3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-oxide is used as an antimicrobial agent for the treatment of bacterial infections. Its beta-lactam structure and antibiotic properties make it a promising candidate for combating various bacterial pathogens.
Used in Research and Development:
In the field of pharmaceutical research and development, this compound can be used as a starting material or a model for the synthesis of new antibiotics with improved properties, such as enhanced efficacy, reduced side effects, or increased resistance to bacterial resistance mechanisms.
Used in Drug Delivery Systems:
Similar to gallotannin, this compound could potentially be incorporated into novel drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. The development of organic and metallic nanoparticles as carriers for this compound could improve its overall effectiveness in treating bacterial infections.

Upstream product

• 132-98-9 penicillin V potassium 
• 1256-06-0 (2S,5R,6R)-benzyl-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 3116-76-5 dicloxacillin 
• 36231-31-9 Dicloxacillin S-sulphoxide 
• 65538-81-0 Penicillin-V-sulfoxid-1'-tert-butylaminocarbonyl-2',2',2'-trichlorethylester 
• 54253-12-2 1ξ-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid cyanomethyl ester 
• 4052-69-1 penicillin-V β-sulfoxide benzyl ester 
• 10213-10-2 sodium tungstate (VI) dihydrate 

Downstream Products

• 40578-83-4 4-(5-methyl-1,3,4-thiadiazole-2-yl)-dithio-3-(2-phenoxyacetamido)-α-isopropenyl-2-oxoazetidine-1-acetic acid 
• 19474-21-6 trichloroethyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide 
• 40578-85-6 2-[2-benzothiazol-2-yldisulfanyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid 
• 75261-30-2 dimethyl 2,2'-dithiobis(α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate) 
• 115203-90-2 2-[(1R,2R)-1-(Benzothiazol-2-yldisulfanyl)-2-carboxy-2-(2-phenoxy-acetylamino)-ethylamino]-3-methyl-but-2-enoic acid methyl ester 
• 22297-57-0 3-Methyl-2-[3-oxo-4-(2-phenoxy-acetylamino)-3H-isothiazol-2-yl]-but-2-enoic acid methyl ester 
• 64370-26-9 methyl (2R,3R)-2-(2'-benzothiazolylthio)-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate 
• 40578-84-5 methyl (2R,3R)-2-(benzothiazol-2'-yldithio)-α-isopropenyl-4-oxo-3-phenoxyacetylaminoazetidine-1-acetate 
• 64370-14-5 (3R,4R)-4-(benzothiazol-2-yl)dithio-3-phenoxyacetamido-2-oxoazetidine 
• 60779-48-8 acetoxymethyl 7-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 
• 22252-43-3 3-deacetyloxy-7-aminocephalosporanic acid 
• 65538-81-0 Penicillin-V-sulfoxid-1'-tert-butylaminocarbonyl-2',2',2'-trichlorethylester 
• 65538-84-3 Penicillin-V-sulfoxid-1'-tert-butylaminocarbonyl-2',2'-dibrompropylester 
• 81244-83-9 acetoxymethyl 6-(phenoxyacetamido)-penicillanate 1-oxide 

Relevant articles and documents

Extremely Selective and Mild Cleavage of β-Haloalkyl Groups by Cobalt(I)phthalocyanine Anion in Semisyntheses of β-Lactam Antibiotics

Cleavage of β-haloalkyl groups can be performed extremely selectively by cobalt(I)phthalocyanine anion under very mild conditions, qualifying it best in the chemistry of highly sensitive β-lactam antibiotics.This is demonstrated in penicillin and cephalosporin semisyntheses.

A mild and convenient synthesis of penicillin and cephalosporin sulfoxides

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Process for the ring expansion of penicillins to cephalosporin compounds

A process for producing a 2-cephem or 3-cephem derivative compound of the formula: SPC1 Wherein R1 represents a substituted or unsubstituted amino radical and R4 represents hydrogen or a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and the dotted line indicates the alternate bond structure providing 3-cephem or 2-cephem, which comprises: Reacting a halogenated derivative selected from the group consisting of a halogenated penam derivative having the formula: SPC2 A halogenated cepham derivative of the formula: SPC3 Wherein X represents a halogen atom, R3 represents a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and R1 is as defined above, or mixtures thereof with a dehydrohalogenoic acid reagent.