GENTAMICIN B

Base Information

• Chemical Name: GENTAMICIN B
• CAS No.: 36889-15-3
• Molecular Formula: C₁₉H₃₈N₄O₁₀
• Molecular Weight: 482.532
• Mol file: 36889-15-3.mol

Synonyms:Betamicin;Gentamicin B; Gentamycin B; Sch 14342

Chemical Property of GENTAMICIN B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 751.2°Cat760mmHg
• Flash Point: 408.1°C
• PSA: 248.39000
• Density: 1.5g/cm³
• LogP: -3.50970

Purity/Quality:

99% ^*data from raw suppliers

GentamicinBDiscontinued,seeG360650 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Antibacterial. Gentamicin B is a derivative of Gentamicin (G360600), an antibiotic from bacteria Micromonospora purpurea and used to treat respiratory and urinary tract, blood, bone and soft tissues infections.

Technology Process of GENTAMICIN B

There total 10 articles about GENTAMICIN B 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: 88.0%

(3R,4R,5R,6R)-5-(benzyloxy)-6-(((1S,2R,3R,4S,6R)-4,6-diazido-3-(((2R,-3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3-methyl-4-(methylamino)tetrahydro-2H-pyran-3-ol → gentamicin B (74464-85-0,36889-15-3)

Guidance literature:

(3R,4R,5R,6R)-5-(benzyloxy)-6-(((1S,2R,3R,4S,6R)-4,6-diazido-3-(((2R,-3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-3-methyl-4-(methylamino)tetrahydro-2H-pyran-3-ol; With sodium hydroxide; trimethylphosphane; In tetrahydrofuran; at 50 ℃; for 2h;

With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid; In tetrahydrofuran; methanol; water; at 20 ℃; for 24h;

DOI:10.1021/jacs.7b09890

Reference yield: 25.0%

(2S)-3,6'-bis-N-benzyloxycarbonyl-1-N-(2-benzyloxycarbonylamino-4-methylpentyloxycarbonyl)gentamicin B (73362-91-1) → gentamicin B (74464-85-0,36889-15-3) + (2S)-1-N-(2-amino-4-methylpentyloxycarbonyl)gentamicin B (73352-77-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium - carbon; In methanol; water; at 25 ℃; for 18h; Pressure (range begins): 55 ;

DOI:10.1039/P19810002186

Reference yield:

→ gentamicin B (74464-85-0,36889-15-3)

Guidance literature:

upstream raw materials:

(2S)-3,6'-bis-N-benzyloxycarbonyl-1-N-(2-benzyloxycarbonylamino-4-methylpentyloxycarbonyl)gentamicin B

C₂₄H₂₆Cl₃NO₆S

C₁₅H₁₉NO₄S

Downstream raw materials:

3,6'-bis-N-benzyloxycarbonylgentamicin B

Refernces

• 1、 Mallams, Alan K.,Morton, James B.,Reichert, Paul. "Semisynthetic Aminoglycoside Antibacterials. Part 10. Synthesis of Novel 1-N-Aminoalkoxycarbonyl and 1-N-Aminoalkylcarboxamido Derivatives of Sisomicin, Gentamicin B, Gentamicin C1a, and Kanamycin A". . p. 2186 - 2208. Retrieved 2007/10/02.
• 2、 -. "Garamine and derivatives thereof". . . Retrieved 2008/06/13.