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Bekanamycin
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Name

Bekanamycin

 EINECS 225-170-5
CAS No. 4696-76-8 Density 1.59g/cm3
PSA 288.40000 LogP -3.82350
Solubility N/A Melting Point 178-182° (dec)
Formula C18H37 N5 O10 Boiling Point 807.7°Cat760mmHg
Molecular Weight 483.519 Flash Point 442.3°C
Transport Information N/A Appearance N/A
Safety Poison by intravenous route. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 4696-76-8 (Bekanamycin) Hazard Symbols N/A
Synonyms

KanamycinB (7CI,8CI); 2'-Amino-2'-deoxykanamycin; Aminodeoxykanamycin; Bekanamycin; KDM;Kanendomycin; NK 1006; Nebramycin V; Nebramycin factor 5

Article Data 2

Bekanamycin Synthetic route

24424-99-5

di-tert-butyl dicarbonate

4696-76-8

kananmycin B

1,3,2',6',3''-penta-N-tert-butoxycarbonyl kanamycin B

Conditions
ConditionsYield
With sodium carbonate In water; isopropyl alcohol at 30℃; for 6h; Temperature;94%
98-59-9

p-toluenesulfonyl chloride

4696-76-8

kananmycin B

60929-91-1, 119818-17-6

1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin B

Conditions
ConditionsYield
With sodium carbonate In ethanol; dichloromethane; water at 25℃; for 16h; Reagent/catalyst; Solvent; Temperature;92.3%
24424-99-5

di-tert-butyl dicarbonate

4696-76-8

kananmycin B

64271-30-3

1,3,2',6',3''-penta-N-BOC-kanamycin B

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 60℃; for 6h;90%
139705-38-7

acetone O-<(vinyloxy)carbonyl>oxime

4696-76-8

kananmycin B

C33H47N5O20

Conditions
ConditionsYield
In phosphate buffer at 0℃; for 5h; pH=8.0;84%
4696-76-8

kananmycin B

207857-15-6

1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine

guanidinoboc10-kanamycin B

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃;80%
4696-76-8

kananmycin B

1268528-26-2

pentaazidokanamycin B

Conditions
ConditionsYield
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
24424-99-5

di-tert-butyl dicarbonate

4696-76-8

kananmycin B

132260-09-4

3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
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;
4696-76-8

kananmycin B

207857-15-6

1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine

320616-55-5

C73H127N15O30

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 72h;65%
108-24-7

acetic anhydride

4696-76-8

kananmycin B

144727-28-6

penta-N-hexa-O-acetylkanamycin B

Conditions
ConditionsYield
With pyridine
104-15-4

toluene-4-sulfonic acid

4696-76-8

kananmycin B

60929-91-1, 119818-17-6

1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin B

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 2h; Ambient temperature;

Bekanamycin Chemical Properties

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 Uses

 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 .

Bekanamycin Toxicity Data With Reference

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.

Bekanamycin Consensus Reports

EPA Genetic Toxicology Program.

Bekanamycin Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.

Bekanamycin Specification

 Bekanamycin (4696-76-8) also can be called Aminodeoxykanamycin and Kanamycin B .

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