Neamine hydrochloride

Base Information

• Chemical Name: Neamine hydrochloride
• CAS No.: 15446-43-2
• Molecular Formula: C12H26 N4 O6 . 4 Cl H
• Molecular Weight: 468.205
• UNII: EIU453IDVS
• Mol file: 15446-43-2.mol

Synonyms:Neamine hydrochloride;15446-43-2;Neamine tetrahydrochloride;EIU453IDVS;Neamine (tetrahydrochloride);Neomycin A Tetrahydrochloride;(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol;tetrahydrochloride;UNII-EIU453IDVS;Neamine (hydrochloride);NEOMYCIN A, TETRAHYDROCHLORIDE;AKOS040755102;2-Deoxy-4-O-(2,6-diaMino-2,6-dideoxy-alpha-D-glucopyranosyl)-D-streptaMine Hydrochloride;HY-115349;CS-0035006;J-009104;Q27277207;(2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-(((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol tetrahydrochloride;D-STREPTAMINE, 2-DEOXY-4-O-(2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL)-, HYDROCHLORIDE (1:4);D-STREPTAMINE, 2-DEOXY-4-O-(2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL)-, TETRAHYDROCHLORIDE

Chemical Property of Neamine hydrochloride

Chemical Property:

• Melting Point: 289 °C (decomp)
• PSA: 203.46000
• LogP: 0.89360
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 468.088995
• Heavy Atom Count: 26
• Complexity: 378

Purity/Quality:

98%Min ^*data from raw suppliers

Neamine hydrochloride ^*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.Cl.Cl.Cl.Cl
• 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.Cl.Cl.Cl.Cl
• Uses: Neamine Hydrochloride is normally found as a core structure of aminoglycoside antibiotics. It is used in the synthesis of disaccharide neamine derivatives as antibacterial agents Neamine is normally found as a core structure of aminoglycoside antibiotics. It is used in the synthesis of disaccharide neamine derivatives as antibacterial agents.

Technology Process of Neamine hydrochloride

There total 4 articles about Neamine hydrochloride 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: 97.0%

neomycin B x sulfate → neamine tetrahydrochloride (15446-43-2)

Guidance literature:

With hydrogenchloride; In methanol; water; for 6h; Reflux;

DOI:10.1002/cbic.201000591

Reference yield: 91.0%

neomycin B (119-04-0) → neamine tetrahydrochloride (15446-43-2)

Guidance literature:

With acetic acid; In water; butan-1-ol;

DOI:10.1016/j.bioorg.2010.10.002

Reference yield: 89.0%

neomycin B sulphate (25389-98-4) → neamine tetrahydrochloride (15446-43-2)

Guidance literature:

With hydrogenchloride; In methanol; water; at 75 ℃; for 16h;

DOI:10.1021/jo062369y

upstream raw materials:

neomycin B

neomycin B sulphate

methanol

Downstream raw materials:

dibenzyl (3aS,4R,5S,7R,7aS)-4-oxohexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

dibenzyl (3aR,4S,5S,7R,7aS)-4-hydroxy-4-vinylhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

dibenzyl (3aR,4S,5S,7R,7aS)-4-allyl-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

dibenzyl (3aR,4S,5S,7R,7aS)-4-(but-3-enyl)-4-hydroxyhexahydrospiro[benzo[d][1,3]dioxole-2,1'-cyclohexane]-5,7-diyldicarbamate

Refernces

• 1、 Andac, Cenk A.,Stringfellow, Thomas C.,Hornemann, Ulfert,Noyanalpan, Ningur. "NMR and amber analysis of the neamine pharmacophore for the design of novel aminoglycoside antibiotics". . p. 28 - 41. Retrieved 2011.
• 2、 Van Den Broek, Sebastiaan A. M. W.,Gruijters, Bas W. T.,Rutjes, Floris P. J. T.,Van Delft, Floris L.,Blaauw, Richard H.. "A short and scalable route to orthogonally O-protected 2-deoxystreptamine". . p. 3577 - 3580. Retrieved 2008/02/04.