(2S)-4-amino-N-[(1R,2R,3R,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5S,6R)-3,4-diamino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-2-hydroxybutanamide

Base Information

• Chemical Name: (2S)-4-amino-N-[(1R,2R,3R,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5S,6R)-3,4-diamino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-2-hydroxybutanamide
• CAS No.: 161822-04-4
• Molecular Formula: C₂₂H₄₆N₈O₈
• Molecular Weight: 550.656
• DSSTox Substance ID: DTXSID10936604
• Nikkaji Number: J596.463F
• Wikidata: Q76279039
• Mol file: 161822-04-4.mol

Synonyms:161822-04-4;2''-Amino-5,2''-dideoxy-5-epiaminoarbekacin;(2S)-4-amino-N-[(1R,2R,3R,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5S,6R)-3,4-diamino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-2-hydroxybutanamide;D-myo-Inositol, O-2,3-diamino-dideoxy-alpha-D-gucopyranosyl-(1-1)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl(1-3)-2,4-diamino-6-((4-amino-2-hydroxy-1-oxobutyl)amino)-2,4,5,6-tetradeoxy-, (S)-;(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-( aminomethyl)oxan-2-yl]oxy-2-[;C22H46N8O8;C22-H46-N8-O8;DTXSID10936604;LS-84054;2''-Amino-2'',5-dideoxy-5-epi-aminoarbekacin;4-Amino-N-{3,5-diamino-2-[(2,3-diamino-2,3-dideoxyhexopyranosyl)oxy]-4-[(2,6-diamino-2,3,4,6-tetradeoxyhexopyranosyl)oxy]cyclohexyl}-2-hydroxybutanimidic acid

Chemical Property of (2S)-4-amino-N-[(1R,2R,3R,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5S,6R)-3,4-diamino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-2-hydroxybutanamide

Chemical Property:

• Vapor Pressure: 8.86E-35mmHg at 25°C
• Boiling Point: 863.6°Cat760mmHg
• Flash Point: 476.1°C
• Density: 1.42g/cm³
• XLogP3: -7.3
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 10
• Exact Mass: 550.34386046
• Heavy Atom Count: 38
• Complexity: 758

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(C(OC1CN)OC2C(CC(C(C2N)OC3C(C(C(C(O3)CO)O)N)N)NC(=O)C(CCN)O)N)N
• Isomeric SMILES: C1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]2[C@H](C[C@H]([C@@H]([C@@H]2N)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)N)NC(=O)[C@H](CCN)O)N)N

Technology Process of (2S)-4-amino-N-[(1R,2R,3R,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5S,6R)-3,4-diamino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-2-hydroxybutanamide

There total 3 articles about (2S)-4-amino-N-[(1R,2R,3R,4R,5S)-3,5-diamino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4R,5S,6R)-3,4-diamino-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexyl]-2-hydroxybutanamide 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:

4'',6'',2'''-tri-O-acetyl-3,2',6',3'',4'''-pentakis(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxy-5-epiazidoarbekacin (161822-11-3) → 2''-amino-5,2''-dideoxy-5-epiaminoarbekacin (161822-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / H₂ / Raney Ni / methanol / 3 h / Ambient temperature

2: 1.) 1M MeONa, 2.) 90percent CF₃COOH/H₂O / 1.) MeOH, r.t., 1 h, 2.) 0 deg C, 1.5 h

With water; hydrogen; sodium methylate; trifluoroacetic acid; nickel; In methanol;

DOI:10.7164/antibiotics.47.821

Reference yield:

4'',6'',2'''-tri-O-acetyl-3,2',6',3'',4'''-pentakis(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-5-O-mesylarbekacin (1055036-39-9) → 2''-amino-5,2''-dideoxy-5-epiaminoarbekacin (161822-04-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaN₃ / dimethylformamide / 3 h / 120 °C

2: 65 percent / H₂ / Raney Ni / methanol / 3 h / Ambient temperature

3: 1.) 1M MeONa, 2.) 90percent CF₃COOH/H₂O / 1.) MeOH, r.t., 1 h, 2.) 0 deg C, 1.5 h

With sodium azide; water; hydrogen; sodium methylate; trifluoroacetic acid; nickel; In methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.47.821

Reference yield:

4'',6'',2'''-tri-O-acetyl-3,2',6',3'',4'''-pentakis(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxy-5-epiaminoarbekacin → 2''-amino-5,2''-dideoxy-5-epiaminoarbekacin (161822-04-4)

Guidance literature:

With water; sodium methylate; trifluoroacetic acid; Yield given. Multistep reaction; 1.) MeOH, r.t., 1 h, 2.) 0 deg C, 1.5 h;

DOI:10.7164/antibiotics.47.821

upstream raw materials:

4'',6'',2'''-tri-O-acetyl-3,2',6',3'',4'''-pentakis(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-5,2''-dideoxy-5-epiazidoarbekacin

4'',6'',2'''-tri-O-acetyl-3,2',6',3'',4'''-pentakis(N-tert-butoxycarbonyl)-2''-(tert-butoxycarbonyl)amino-2''-deoxy-5-O-mesylarbekacin

Refernces