Bekanamycin

Base Information

• Chemical Name: Bekanamycin
• CAS No.: 4696-76-8
• Molecular Formula: C18H37 N5 O10
• Molecular Weight: 483.519
• European Community (EC) Number: 225-170-5
• UNII: 15JT14C3GI
• DSSTox Substance ID: DTXSID8023185
• Nikkaji Number: J8.763G
• Wikipedia: Bekanamycin
• Wikidata: Q3637540
• NCI Thesaurus Code: C65248
• Metabolomics Workbench ID: 51585
• ChEMBL ID: CHEMBL176
• Mol file: 4696-76-8.mol

Synonyms:aminodeoxykanamycin;bekanamycin;bekanamycin sulfate;bekanamycin sulfate (1:1);kanamycin B;kanendomycin

Chemical Property of Bekanamycin

Chemical Property:

• Vapor Pressure: 3.43E-30mmHg at 25°C
• Melting Point: 178-182° (dec)
• Refractive Index: 1.7600 (estimate)
• Boiling Point: 807.7°Cat760mmHg
• PKA: 13.07±0.70(Predicted)
• Flash Point: 442.3°C
• PSA: 288.40000
• Density: 1.59g/cm³
• LogP: -3.82350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Aqueous Acid (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Sparingl
• XLogP3: -7.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 483.25404239
• Heavy Atom Count: 33
• Complexity: 639

Purity/Quality:

97% ^*data from raw suppliers

Kanamycin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)N)N
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
• Uses: Kanamycin B (cas# 4696-76-8) is a compound useful in organic synthesis.

Technology Process of Bekanamycin

There total 1 articles about Bekanamycin 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:

→ kananmycin B (4696-76-8)

Guidance literature:

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + kananmycin B (4696-76-8) → 1,3,2',6',3''-penta-N-tert-butoxycarbonyl kanamycin B

Guidance literature:

With sodium carbonate; In water; isopropyl alcohol; at 30 ℃; for 6h; Temperature;

Reference yield: 92.3%

p-toluenesulfonyl chloride (98-59-9) + kananmycin B (4696-76-8) → kanamycin B 1,3,2',6',3''-penta-p-toluenesulfonate (60929-91-1,119818-17-6)

Guidance literature:

With sodium carbonate; In ethanol; dichloromethane; water; at 25 ℃; for 16h; Reagent/catalyst; Solvent; Temperature;

Downstream raw materials:

3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B

1,3,2',6',3''-penta-N-BOC-kanamycin B

penta-N-hexa-O-acetylkanamycin B

N,N'-bis-benzyloxycarbonyl-O⁴-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine

Refernces

New Derivatives of Kanamycin B Obtained by Modifications and Substitutions in Position 6''. 1. Synthesis and Microbiological Evaluation

10.1021/jm00108a035

This research aimed to explore the impact of modifying the hydrophobic/hydrophilic balance at a specific site of an aminoglycoside antibiotic, specifically kanamycin B, by chemically modifying its 6" position through substitution with various groups including halogens, pseudohalogens, amino, amido, thioalkyl, and alkoxy groups. The study sought to understand how these modifications affected the antibacterial activity and toxicity of the derivatives. The conclusions drawn from the research indicated that only derivatives with small substituents in position 6", such as chloro, bromo, azido, amino, and methylcarbamido, showed acceptable antibacterial activity. A negative correlation was observed between the size of the 6" substituent and antibacterial activity against both Gram-positive and Gram-negative organisms sensitive to kanamycin B. The chemicals used in the process included kanamycin B, tert-butoxycarbonyl (BOC) as an N-protective group, 2,4,6-triisopropylbenzenesulfonyl chloride (TIBS-Cl) for sulfonylation, various nucleophiles for substitution reactions, and a range of reagents for the synthesis of different 6"-substituted kanamycin B derivatives.