Gentamicin C1

Base Information

• Chemical Name: Gentamicin C1
• CAS No.: 25876-10-2
• Deprecated CAS: 1120351-21-4,1120351-23-6,1120351-24-7,1260781-82-5
• Molecular Formula: C₂₁H₄₃N₅O₇
• Molecular Weight: 477.602
• European Community (EC) Number: 215-765-8
• UNII: I904Y9FPPV
• DSSTox Substance ID: DTXSID9023091
• Nikkaji Number: J37.113K
• Wikipedia: Gentamicin
• Wikidata: Q27280589
• NCI Thesaurus Code: C76148
• RXCUI: 1596450
• Metabolomics Workbench ID: 67882
• ChEMBL ID: CHEMBL463809
• Mol file: 25876-10-2.mol

Synonyms:gentamicin C;gentamicin C sulfate;gentamicin C1;gentamicin C1 sulfate;gentamicin C1 sulfate (5:2);gentamicin C1a;gentamicin C2;gentamicin C2a;Sch 13706

Chemical Property of Gentamicin C1

Chemical Property:

• Vapor Pressure: 8.85E-21mmHg at 25°C
• Melting Point: 125-130°C
• Boiling Point: 669.4°C at 760 mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 358.6°C
• PSA: 199.73000
• Density: 1.3g/cm³
• LogP: -0.44480
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly, Sonicated)
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 477.31624873
• Heavy Atom Count: 33
• Complexity: 636

Purity/Quality:

99% ^*data from raw suppliers

Gentamicin C1 pentaacetate salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Aminoglycosides
• Canonical SMILES: CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
• Isomeric SMILES: C[C@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@](CO3)(C)O)NC)O)N)N)N)NC
• Recent ClinicalTrials: Intramedullary Calcium Sulfate Antibiotic Depot
• Recent EU Clinical Trials: Short or Long Antibiotic Regimes in Orthopaedics (SOLARIO):
• Recent NIPH Clinical Trials: An open-label randomized controlled trial of ampicillin/cloxacillin and ceftriaxone for empirical treatment of infective endocarditis
• Uses: Gentamicin C1 is an intermediate in the synthesis of Gentamicin C2 Pentaacetate Salt (Mixture of C2 and C2a) (G360595), which is an antibacterial. A mixture of Gentamicin C2 and Gentamycin C2a.

Technology Process of Gentamicin C1

There total 2 articles about Gentamicin C1 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:

3,2'-bis-N-trifluoroacetylgentamicin C1 (54619-80-6) → 1-epi-gentamicin C1 (25876-10-2,51819-90-0,61117-71-3,79298-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 3,5-di-t-butyl-1,2-benzoquinone, 1M-sulphuric acid / methanol / 28 h / 25 °C / pH = 2.5 - 3.0

2: 1.) ammonium chloride, sodium cyanoborohydride, ammonia, 2.) conc. ammonium hydroxide / 1.) methanol, pH = 5.5 - 6, 25 deg C, 20 h, 2.) 25 deg C, 72 h

With ammonium hydroxide; sulfuric acid; 3,5-di-tert-butyl-o-benzoquinone; ammonium chloride; sodium cyanoborohydride; In methanol;

DOI:10.1039/P19810002168

Reference yield:

N-{(1S,2R,3S,4R)-4-((2R,3R,4R,5R)-3,5-Dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-2-[(2R,3R,6S)-6-(1-methylamino-ethyl)-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-5-oxo-cyclohexyl}-2,2,2-trifluoro-acetamide; compound with sulfuric acid (66065-90-5) → gentamicin C1 (287730-69-2) + 1-epi-gentamicin C1 (25876-10-2,51819-90-0,61117-71-3,79298-85-4) + 1-deamino-1-hydroxygentamicin C1 (66065-94-9,66101-44-8) + 1-deamino-1-epi-hydroxygentamicin C1 (66065-94-9,66101-44-8)

Guidance literature:

With ammonium hydroxide; ammonium chloride; sodium cyanoborohydride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) methanol, pH = 5.5 - 6, 25 deg C, 20 h, 2.) 25 deg C, 72 h;

DOI:10.1039/P19810002168

upstream raw materials:

N-{(1S,2R,3S,4R)-4-((2R,3R,4R,5R)-3,5-Dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-2-[(2R,3R,6S)-6-(1-methylamino-ethyl)-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yloxy]-5-oxo-cyclohexyl}-2,2,2-trifluoro-acetamide; compound with sulfuric acid

3,2'-bis-N-trifluoroacetylgentamicin C₁

Refernces