4-Amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside

Base Information

• Chemical Name: 4-Amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside
• CAS No.: 56391-56-1
• Molecular Formula: C21H41 N5 O7
• Molecular Weight: 475.586
• European Community (EC) Number: 260-146-8
• DSSTox Substance ID: DTXSID30860699
• Wikipedia: Netilmicin
• Mol file: 56391-56-1.mol

Synonyms:4-amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside;56391-56-1;Prestwick0_001101;Prestwick1_001101;Prestwick2_001101;SPBio_003081;DTXSID30860699;BBL033848;STL372906;AKOS015961227;AC-13442;VS-12312;FT-0696361;2-[(4-amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl)oxy]-5-methyl-4-(methylamino)oxane-3,5-diol

Chemical Property of 4-Amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside

Chemical Property:

• Vapor Pressure: 1.1E-21mmHg at 25°C
• Refractive Index: 1.7500 (estimate)
• Boiling Point: 684.3°Cat760mmHg
• PKA: 13.29±0.70(Predicted)
• Flash Point: 367.7°C
• PSA: 199.73000
• Density: 1.32g/cm³
• LogP: -0.31800
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 475.30059866
• Heavy Atom Count: 33
• Complexity: 673

Purity/Quality:

99% ^*data from raw suppliers

Netilmicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCNC1CC(C(C(C1OC2C(C(C(CO2)(C)O)NC)O)O)OC3C(CC=C(O3)CN)N)N
• Description: This is a semisynthetic derivative of sisomicin, which was developed by ethylation of the 1-N position of the deoxystreptamine ring of sisomicin . Clinically, netilmicin is used as a sulfate. Netilmicin has a similar in vitro antibacterial spectrum to that of gentamicin but, unlike sisomicin, it is active against a proportion of gentamicin-resistant Gram-negative bacilli. However, netilmicin is not active against as wide a range of gentamicin-resistant Gram-negative bacilli as amikacin. Nevertheless, it may be occasionally indicated as an alternative to amikacin for the treatment of infections caused by gentamicin-resistant but netilmicin-susceptible Gram-negative organisms. The following details apply only to netilmicin
• Therapeutic Function: Antibiotic
• Clinical Use: Severe infections (including septicemia, lower respiratory tract infections, urinary tract infections, peritonitis, endometritis) caused by susceptible strains of Gram-negative bacilli and staphylococci
• Drug interactions: Netilmicin is inactivated less than gentamicin and tobramycin by high concentrations of various penicillins . At the highest penicillin concentration studied (500 mg/ml), inactivation of netilmicin was a little higher than amikacin. The in vivo inactivation of netilmicin was compared with gentamicin in patients with end-stage renal disease. The terminal elimination half-life for gentamicin decreased from 60 to 25 hours, whereas the values for netilmicin remained essentially the same at 42 to 40 hours. Such patients receiving combinations of netilmicin and various penicillins will not require further dose adjustment. Netilmicin differed from other aminoglycosides by reducing T3 or triiodothyroxime levels in serum.

Technology Process of 4-Amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside

There total 7 articles about 4-Amino-3-{[3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy}-6-(ethylamino)-2-hydroxycyclohexyl 3-deoxy-4-c-methyl-3-(methylamino)pentopyranoside 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: 90.0%

2',3,6'-tri-N-acetyl-1-N-ethylsisomicin (66567-31-5) → netilmicin (56391-56-1)

Guidance literature:

With sodium hydroxide; for 48h; Heating;

DOI:10.1016/0008-6215(84)85282-9

Reference yield: 19.0%

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide (66567-31-5) → 1-deamino-1-hydroxysisomicin (66065-95-0,66101-45-9) + 1-deamino-1-epi-hydroxysisomicin (66065-95-0,66101-45-9) + netilmicin (56391-56-1) + 1-epi-N-ethylsisomicin (67650-39-9)

Guidance literature:

With sodium hydroxide; for 50h; Further byproducts given; Heating;

DOI:10.1039/P19810002168

Reference yield: 10.0%

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide (66567-31-5) → sisomicin (32385-11-8) + 1-deamino-1-hydroxysisomicin (66065-95-0,66101-45-9) + netilmicin (56391-56-1) + 1-epi-N-ethylsisomicin (67650-39-9)

Guidance literature:

With sodium hydroxide; for 50h; Further byproducts given; Heating;

DOI:10.1039/P19810002168

upstream raw materials:

N-[(1S,2R,3S,4S)-2-[(2S,3R)-3-Acetylamino-6-(acetylamino-methyl)-3,4-dihydro-2H-pyran-2-yloxy]-4-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-5-ethylamino-3-hydroxy-cyclohexyl]-acetamide

2',3,6'-tri-N-acetyl-1-N-ethylsisomicin

sisomicin

3,2',6'-tri-N-acetylsisomicin

Refernces

• 1、 Nagabhushan, Tattanahalli L.,Turner, William N.,Tsai, Hsinghan,Jaret, Robert S.,Schumacher, Doris,et al.. "THE SYNTHESIS OF NETILMICIN via COMPLEXING OF VICINAL AND NON-VICINAL AMINO-HYDROXYL GROUP PAIRS WITH DIVALENT TRANSITION-METAL CATIONS". . p. 243 - 250. Retrieved 2007/10/02.