Dibekacin

Base Information

• Chemical Name: Dibekacin
• CAS No.: 34493-98-6
• Molecular Formula: C18H37 N5 O8
• Molecular Weight: 451.52
• European Community (EC) Number: 252-064-6
• UNII: 45ZFO9E525
• DSSTox Substance ID: DTXSID2022915
• Nikkaji Number: J94.714H
• Wikipedia: Dibekacin
• Wikidata: Q3706873
• NCI Thesaurus Code: C79114
• Metabolomics Workbench ID: 55733
• ChEMBL ID: CHEMBL560976
• Mol file: 34493-98-6.mol

Synonyms:3',4' Dideoxykanamycin B;3',4'-Dideoxykanamycin B;B, 3',4'-Dideoxykanamycin;Dibekacin;Dibekacin Sulfate;Dibekacin Sulphate;Dideoxykanamycin B;Dideoxykanamycine;Orbicin;Sulfate, Dibekacin;Sulphate, Dibekacin

Chemical Property of Dibekacin

Chemical Property:

• Appearance/Colour: yellowish powder
• Vapor Pressure: 1.9E-24mmHg at 25°C
• Refractive Index: 1.7600 (estimate)
• Boiling Point: 727.7 °C at 760 mmHg
• PKA: 13.07±0.70(Predicted)
• Flash Point: 393.9 °C
• PSA: 253.73000
• Density: 1.46 g/cm³
• LogP: -1.09840
• XLogP3: -5.8
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 451.26421316
• Heavy Atom Count: 31
• Complexity: 579

Purity/Quality:

99% ^*data from raw suppliers

DIBEKACIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(OC1CN)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CO)O)N)O)N)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]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N)N)N
• Uses: Dideoxykanamycin B is an antibacterial compound.
• Therapeutic Function: Antibacterial

Technology Process of Dibekacin

There total 25 articles about Dibekacin 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: 98.0%

3',4'-dideoxy-3',4'-didehydro kanamycin B (63770-47-8) → dibecacin (34493-98-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In water;

DOI:10.1016/0008-6215(82)84044-5

Reference yield: 70.0%

penta-N-acetyldibekacin (108050-24-4) → dibecacin (34493-98-6)

Guidance literature:

With hydrazine hydrate; at 100 ℃; for 72h;

DOI:10.1248/cpb.35.2136

Reference yield: 1.0%

O-3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1->6)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1a (79384-36-4) → dibecacin (34493-98-6)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -80 ℃; for 0.75h;

DOI:10.1039/P19810002137

upstream raw materials:

3',4'-dideoxy-3',4'-didehydro kanamycin B

O-3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1->6)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C_1a

penta-N-acetyldibekacin

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

Downstream raw materials:

1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin B

3',4'-dideoxy-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)kanamycin B

Refernces

• 1、 Yoshikawa,Torihara,Nakae,Cha,Kitagawa. "Synthesis of dibekacin (3',4'-dideoxykanamycin B) from D-glucosamine and D-glucose.". . p. 2136 - 2139. Retrieved 2007/10/02.
• 2、 Daniels, Peter J. L.,Luce, Charles E.,Mallams, Alan K.,Morton, James B.,Saluja, Surinderjit S.,at al.. "Semisynthetic Aminoglycoside Antibacterials. Part 7. Synthesis of Novel Hexopyranosyl and Hexofuranosyl Derivatives of Gentamine C1 and C1a". . p. 2137 - 2150. Retrieved 2007/10/02.