cephalosporin C

Base Information

• Chemical Name: cephalosporin C
• CAS No.: 61-24-5
• Molecular Formula: C16H21 N3 O8 S
• Molecular Weight: 415.424
• European Community (EC) Number: 200-501-6,254-669-0
• UNII: 3XIY7HJT5L
• DSSTox Substance ID: DTXSID90960427
• Nikkaji Number: J4.815A
• Wikipedia: Cephalosporin_C
• Wikidata: Q5063335
• Metabolomics Workbench ID: 50256
• ChEMBL ID: CHEMBL482858
• Mol file: 61-24-5.mol

Synonyms:cephalosporin C;cephalosporin C hydrochloride;cephalosporin C, monosodium salt;cephalosporin C, monosodium salt, (6R-(6alpha,7beta))-isomer;cephalosporin C, monozinc salt;cephalosporin C, potassium salt;cephalosporin C, potassium salt, (6R-(6alpha,7beta(S*)))-isomer;cephalosporin C, sodium salt;cephalosporin C, sodium salt, (6R-(6alpha,7beta))-isomer;cephalosporin C, zinc salt

Chemical Property of cephalosporin C

Chemical Property:

• Vapor Pressure: 3.38E-29mmHg at 25°C
• Boiling Point: 814.7°C at 760 mmHg
• PKA: 2.49±0.24(Predicted)
• Flash Point: 446.5°C
• PSA: 201.63000
• Density: 1.55±0.1 g/cm3(Predicted)
• LogP: -0.10060
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 415.10493581
• Heavy Atom Count: 28
• Complexity: 737

Purity/Quality:

99% ^*data from raw suppliers

(6R,7R)-3-[(ACETYLOXY)METHYL]-7-[[(5R)-5-AMINO-5-CARBOXYPENTANOYL]AMINO]-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CCCC(C(=O)O)N)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CCC[C@H](C(=O)O)N)SC1)C(=O)O
• Recent ClinicalTrials: Trial of Randomized Antibiotic Administration in Percutaneous Nephrolithotomy

Refernces

STEREOSELECTIVE ONE-POT SYNTHESES OF TRANS-3-AMINO-β-LACTAMS FROM ZINC ENOLATES OF N-PROTECTED α-AMINOACID ESTERS AND IMINES

10.1016/S0040-4039(00)87909-5

The study in the literature presents a new one-pot synthesis method for 3-amino-β-lactams, which are valuable intermediates for producing various β-lactam antibiotics, including penicillins and cephalosporins. The key chemicals involved are zinc enolates derived from N-protected amino acid esters and imines. Specifically, the zinc enolates are prepared in situ from the corresponding lithium enolates via transmetallation with zinc dichloride. These enolates then react with imines to form the desired 3-amino-β-lactams. The study highlights the high yields and trans-stereoselectivity of this synthetic route, which contrasts with reactions involving lithium enolates. The authors also note that the enolates derived from 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetic acid ethyl ester (STABASE) are more stable and yield better results than those from N,N-bis(trimethylsilyl)glycine ethyl ester. The study provides detailed procedures and characterizations of the synthesized compounds, and it suggests that the trans-stereoselectivity arises from a rigid cyclic chair-like transition state of the enolate with an E-imine.