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CAS No.: | 4696-76-8 |
---|---|
Name: | Bekanamycin |
Article Data: | 2 |
Molecular Structure: | |
Formula: | C18H37 N5 O10 |
Molecular Weight: | 483.519 |
Synonyms: | KanamycinB (7CI,8CI); 2'-Amino-2'-deoxykanamycin; Aminodeoxykanamycin; Bekanamycin; KDM;Kanendomycin; NK 1006; Nebramycin V; Nebramycin factor 5 |
EINECS: | 225-170-5 |
Density: | 1.59g/cm3 |
Melting Point: | 178-182° (dec) |
Boiling Point: | 807.7°Cat760mmHg |
Flash Point: | 442.3°C |
Safety: | Poison by intravenous route. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. |
PSA: | 288.40000 |
LogP: | -3.82350 |
di-tert-butyl dicarbonate
kananmycin B
Conditions | Yield |
---|---|
With sodium carbonate In water; isopropyl alcohol at 30℃; for 6h; Temperature; | 94% |
p-toluenesulfonyl chloride
kananmycin B
1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin B
Conditions | Yield |
---|---|
With sodium carbonate In ethanol; dichloromethane; water at 25℃; for 16h; Reagent/catalyst; Solvent; Temperature; | 92.3% |
di-tert-butyl dicarbonate
kananmycin B
1,3,2',6',3''-penta-N-BOC-kanamycin B
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide at 60℃; for 6h; | 90% |
Conditions | Yield |
---|---|
In phosphate buffer at 0℃; for 5h; pH=8.0; | 84% |
kananmycin B
1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water at 20℃; | 80% |
kananmycin B
pentaazidokanamycin B
Conditions | Yield |
---|---|
With triflic azide; triethylamine; zinc(II) chloride In methanol; water at 20℃; Inert atmosphere; | 76% |
Stage #1: kananmycin B With copper(II) sulfate In water for 0.25h; Stage #2: With triethylamine In water for 0.333333h; Cooling with ice; Further stages; | 1.66 g |
di-tert-butyl dicarbonate
kananmycin B
3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B
Conditions | Yield |
---|---|
Stage #1: kananmycin B With zinc(II) acetate dihydrate In dimethyl sulfoxide at 21℃; Stage #2: di-tert-butyl dicarbonate In dimethyl sulfoxide at 21℃; for 5h; | 66% |
With zinc diacetate 1.) DMSO, RT, overnight, 2.) 5 h; Yield given. Multistep reaction; |
kananmycin B
1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine
C73H127N15O30
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water at 20℃; for 72h; | 65% |
Conditions | Yield |
---|---|
With pyridine |
toluene-4-sulfonic acid
kananmycin B
1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin B
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 2h; Ambient temperature; |
Molecular Formula: C18H37N5O10
Molar mass: 483.5139 g/mol
EINECS: 225-170-5
Density: 1.59 g/cm3
Flash Point: 442.3 °C
Index of Refraction: 1.668
Boiling Point: 807.7 °C at 760 mmHg
Vapour Pressure: 3.43E-30 mmHg at 25°C
Product categories of Bekanamycin (4696-76-8): Pharmaceutical Intermediates
Structure of Bekanamycin (4696-76-8):
XLogP3-AA: -7.2
H-Bond Donor: 11
H-Bond Acceptor: 15
IUPAC Name: (2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4-diol
Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(C(C(C(O3)CN)O)O)N)N
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)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N
InChI: InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1
InChIKey: SKKLOUVUUNMCJE-FQSMHNGLSA-N
Bekanamycin (4696-76-8) has been used for the antibiotic medicine, and is also used as the intermediates of the production of Sulfuric acid in the Bekaa star and Arbekacin .
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 800mg/kg (800mg/kg) | "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 159, 1980. | |
mouse | LD50 | intravenous | 132mg/kg (132mg/kg) | Journal of Antibiotics. Vol. 27, Pg. 677, 1974. | |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 1901, 1969. | |
mouse | LD50 | subcutaneous | 750mg/kg (750mg/kg) | "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 159, 1980. | |
rat | LD50 | intramuscular | 1420mg/kg (1420mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 1901, 1969. | |
rat | LD50 | intraperitoneal | 1400mg/kg (1400mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 1901, 1969. | |
rat | LD50 | intravenous | 141mg/kg (141mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 1901, 1969. | |
rat | LD50 | oral | > 10gm/kg (10000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 1901, 1969. | |
rat | LD50 | subcutaneous | 1900mg/kg (1900mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 1901, 1969. |
EPA Genetic Toxicology Program.
Poison by intravenous route. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.
Bekanamycin (4696-76-8) also can be called Aminodeoxykanamycin and Kanamycin B .