Gentamicin C1a

Base Information

• Chemical Name: Gentamicin C1a
• CAS No.: 26098-04-4
• Deprecated CAS: 58207-27-5
• Molecular Formula: C19H39 N5 O7
• Molecular Weight: 449.548
• Hs Code.: 3004909090
• UNII: AV4A72IATD
• DSSTox Substance ID: DTXSID4023092
• Nikkaji Number: J17.060G
• Wikidata: Q27095468
• NCI Thesaurus Code: C76149
• Metabolomics Workbench ID: 51456
• ChEMBL ID: CHEMBL194126
• Mol file: 26098-04-4.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 C1a

Chemical Property:

• Vapor Pressure: 3.97E-21mmHg at 25°C
• Melting Point: 102-108oC
• Boiling Point: 675.2°C at 760 mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 362.1°C
• PSA: 213.72000
• Density: 1.36g/cm³
• LogP: -0.78460
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 449.28494860
• Heavy Atom Count: 31
• Complexity: 592

Purity/Quality:

99%, ^*data from raw suppliers

Gentamicin C1a Pentaacetate Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(CCC(O3)CN)N)N)N)O
• Isomeric SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H](CC[C@H](O3)CN)N)N)N)O

Technology Process of Gentamicin C1a

There total 4 articles about Gentamicin C1a 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%

C19H31N13O7 → Gentamicin C1a (26098-04-4)

Guidance literature:

With sodium hydroxide; water; trimethylphosphane; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmc.2008.08.053

Reference yield:

C20H37N5O8 → Gentamicin C1a (26098-04-4)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 80 ℃; for 3h;

Reference yield:

sisomicin (32385-11-8) → Gentamicin C1a (26098-04-4) + micronomicin (52093-21-7)

Guidance literature:

In water; at 30 ℃; for 20h; Micromonospora sagamiensis KY 11525, pH 7.5;

DOI:10.1080/00021369.1982.10865090

upstream raw materials:

sisomicin

Downstream raw materials:

tert-butyl (1S,2R,3R,4S,5R)-5-amino-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-3-hydroxy-2-((2R,3R,6S)-3-(2-nitrophenylsulfonamido)-6-((2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-2-yloxy)cyclohexylcarbamate

tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-ieri-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-4-tert-butoxycarbonylaminobutanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitrophenylsulfonamido)methyl)tetrahydro-2H-pyran-3-ylcarbamate

(S)-3-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-((2R,3R,6S)-3-amino-6-((2-hydroxyethylamino)methyl)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-3-hydroxycyclohexyl)-2-hydroxypropanamide

tert-butyl (2R,3R,6S)-2-((1R,2SS,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(N-methyl-tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxy-4-((S)-2-hydroxy-3-tert-butoxycarbonylaminopropanamido)-6-tert-butoxycarbonylaminocyclohexyloxy)-6-((2-(tetrahydro-2H-pyran-2-yloxy)ethylamino)methyl)tetrahydro-2H-pyran-3-ylcarbamate

Refernces

• 1、 Chen, Lilach,Hainrichson, Mariana,Bourdetsky, Dmitry,Mor, Amram,Yaron, Sima,Baasov, Timor. "Structure-toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds". experimental part. p. 8940 - 8951. Retrieved 2009/04/03.