Cephaloglycin

Base Information

• Chemical Name: Cephaloglycin
• CAS No.: 3577-01-3
• Molecular Formula: C18H19 N3 O6 S
• Molecular Weight: 405.431
• European Community (EC) Number: 222-696-7
• UNII: HD2D469W6U
• DSSTox Substance ID: DTXSID4022781
• Nikkaji Number: J3.406A
• Wikipedia: Cefaloglycin
• Wikidata: Q5057214
• NCI Thesaurus Code: C76593
• Metabolomics Workbench ID: 43002
• ChEMBL ID: CHEMBL1200971
• Mol file: 3577-01-3.mol

Synonyms:Cefaloglycin;Cephaloglycin;Cephaloglycin Dihydrate;Cephaloglycine;Dihydrate, Cephaloglycin

Chemical Property of Cephaloglycin

Chemical Property:

• Vapor Pressure: 2.14E-24mmHg at 25°C
• Melting Point: 236.5°C (rough estimate)
• Refractive Index: 1.6390 (estimate)
• Boiling Point: 761.8°C at 760 mmHg
• PKA: pKa 1.71(H2O t=25±2 I=0.1 ) (Uncertain);7.29(H2O t=25±2 I=0.1 ) (Uncertain)
• Flash Point: 414.5°C
• PSA: 164.33000
• Density: 1.52g/cm³
• LogP: 1.01720
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: 10.5g/L(25 oC)
• XLogP3: -3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 405.09945651
• Heavy Atom Count: 28
• Complexity: 718

Purity/Quality:

99%, ^*data from raw suppliers

Cephaloglycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O
• Uses: Cefaloglycin is a first-generation cephalosporin antibiotic. Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Cephaloglycin

There total 5 articles about Cephaloglycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

→ cephaloglycin (3577-01-3)

Guidance literature:

Reference yield:

D-phenylglycine methyl ester hydrochloride (19883-41-1,13226-98-7) + 7-Aminocephalosporanic acid (957-68-6) → cephaloglycin (3577-01-3)

Guidance literature:

With potassium phosphate; Pseudomonas melanogenum KY 8541; at 30 ℃; pH=6.5;

DOI:10.1248/cpb.37.315

Reference yield:

(6R)-3-acetoxymethyl-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7765-60-8) → cephaloglycin (3577-01-3)

Guidance literature:

Multistep reaction; (i) CF3CO2H, (ii) ion exchange resin - form>;

DOI:10.1021/jm00323a024

upstream raw materials:

(6R)-3-acetoxymethyl-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(R)-Phenylglycine methyl ester

7-Aminocephalosporanic acid

D-phenylglycine methyl ester hydrochloride

Downstream raw materials:

(6R)-3-acetoxymethyl-8-oxo-7t-[(R)-2-(1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonylamino)-2-phenyl-acetylamino]-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-3-acetoxymethyl-7t-[(R)-2-((Ξ)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonylamino)-2-phenyl-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-3-acetoxymethyl-7t-{(R)-2-[8-(4-formyl-piperazin-1-yl)-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carbonylamino]-2-phenyl-acetylamino}-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R)-3-acetoxymethyl-8-oxo-7t-[(R)-2-(6-oxo-1,2-dihydro-6H-pyrrolo[3,2,1-ij]quinoline-5-carbonylamino)-2-phenyl-acetylamino]-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 Ogasa,Saito,Hashimoto,Sato,Hirata. "Synthesis and biological evaluation of optically active 3-H-1 carbacephem compounds". . p. 315 - 321. Retrieved 2007/10/02.
• 2、 Spencer,Flynn,Roeske,Siu,Chauvette. "Chemistry of cephalosporin antibiotics. VII. Synthesis of cephaloglycin and some homologs.". . p. 746 - 750. Retrieved 2007/10/07.