Neamine

Base Information

• Chemical Name: Neamine
• CAS No.: 3947-65-7
• Molecular Formula: C12H26 N4 O6
• Molecular Weight: 322.362
• UNII: 5981U00LY0
• DSSTox Substance ID: DTXSID7023358
• Nikkaji Number: J4.461J
• Wikipedia: Neamine
• Wikidata: Q6984256
• NCI Thesaurus Code: C76155
• Metabolomics Workbench ID: 50011
• ChEMBL ID: CHEMBL427409
• Mol file: 3947-65-7.mol

Synonyms:neamin;neamine;neomycin A

Chemical Property of Neamine

Chemical Property:

• Vapor Pressure: 9.19E-16mmHg at 25°C
• Melting Point: 225.5°C (rough estimate)
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 577.9°C at 760 mmHg
• PKA: 13.24±0.70(Predicted)
• Flash Point: 303.3°C
• PSA: 203.46000
• Density: 1.51g/cm³
• LogP: -2.31440
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: Aqueous Acid (Slightly), Methanol (Slightly, Heated), Water (Slightly)
• XLogP3: -5.4
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 322.18523456
• Heavy Atom Count: 22
• Complexity: 378

Purity/Quality:

98%Min ^*data from raw suppliers

Neamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)O)O)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)CN)O)O)N)O)O)N
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Technology Process of Neamine

There total 20 articles about Neamine 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: 91.0%

(1S,2R,3R,4S,6R)-4,6-Diamino-3-((2R,3R,4R,5R,6R)-3-amino-6-aminomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol (549501-35-1) → neomycin A (3947-65-7)

Guidance literature:

With hydrogen; 20% palladium hydroxide on carbon; In water; acetic acid;

Reference yield: 82.0%

neomycin B (119-04-0) → neomycin A (3947-65-7)

Guidance literature:

With hydrogenchloride; In methanol; for 6h; Heating;

DOI:10.1021/ja9612817

Reference yield: 70.0%

neomycin B trisulfate → neomycin A (3947-65-7)

Guidance literature:

neomycin B trisulfate; With hydrogenchloride; In methanol; for 6h; Heating;

With ammonium hydroxide; ammonia; In methanol; Further stages.;

DOI:10.1021/jo0707636

upstream raw materials:

neomycin B sulphate

neomycin B

(1S,2R,3R,4S,6R)-4,6-Diamino-3-((2R,3R,4R,5R,6R)-3-amino-6-aminomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

Downstream raw materials:

N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine

{(1R,2S,3R,4R,5S)-4-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-3-vinyloxycarbonylamino-6-(vinyloxycarbonylamino-methyl)-tetrahydro-pyran-2-yloxy]-2,3-dihydroxy-5-vinyloxycarbonylamino-cyclohexyl}-carbamic acid vinyl ester

C₂₄H₄₇N₅O₁₀

C₂₉H₃₉N₅O₉

Refernces

• 1、 Carter,H.E. et al.. "". . p. 3723 - 3724. Retrieved 1961.
• 2、 Prado, Wiliam A.,Rossaneis, Ana C.,Carvalho, Ivone,Zamoner, Luis Otvio B.,Corrado, Alexandre P.. "Neamine and 2-deoxystreptamine neomycin derivatives exhibit antinociceptive activity in rat models of phasic, incision and neuropathic pain". . p. 1696 - 1704. Retrieved 2016/01/26.