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DIBEKACIN
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Name

DIBEKACIN

 EINECS 252-064-6
CAS No. 34493-98-6 Density 1.46 g/cm3
PSA 253.73000 LogP -1.09840
Solubility N/A Melting Point N/A
Formula C18H37 N5 O8 Boiling Point 727.7 °C at 760 mmHg
Molecular Weight 451.52 Flash Point 393.9 °C
Transport Information N/A Appearance yellowish powder
Safety Poison by intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. An antibacterial agent. When heated to decomposition it emits toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 34493-98-6 ((2R,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol) Hazard Symbols N/A
Synonyms

3',4'-DideoxykanamycinB; DKB; Debecacin; Dibekacin; Dideoxykanamycin B

Article Data 9

DIBEKACIN Synthetic route

63770-47-8

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

34493-98-6

dibecacin

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In water98%
With platinum(IV) oxide; hydrogen; acetic acid In water at 20℃; for 24h; Temperature;96%
108050-24-4

penta-N-acetyldibekacin

34493-98-6

dibecacin

Conditions
ConditionsYield
With hydrazine hydrate at 100℃; for 72h;70%
79384-36-4

O-3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1->6)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1a

34493-98-6

dibecacin

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -80℃; for 0.75h;1%

N-[(2S,5R,6R)-5-Amino-6-((3aS,4R,5S,7R,7aS)-5,7-diamino-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yloxy)-tetrahydro-pyran-2-ylmethyl]-acetamide

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: Na2CO3 / H2O; dioxane
2: 80 percent aq. AcOH / 60 °C
3: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
4: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
5: methanol
6: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
7: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme

(2R,3S,4S,5R,6R)-4-(2,4-Dinitro-phenylamino)-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,5-diol

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: BaO, Ba(OH)2*8H2O / dimethylformamide
2: 6 N aq. HCl, AcOH / 90 °C
3: 25 percent HBr / CHCl3 / 5 °C
4: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
5: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
6: methanol
7: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
8: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme
113922-91-1

{(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

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
2: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
3: methanol
4: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
5: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme

{(3aS,4R,5S,7R,7aS)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-ethoxycarbonylamino-tetrahydro-pyran-2-yloxy]-7-ethoxycarbonylamino-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid ethyl ester

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80 percent aq. AcOH / 60 °C
2: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
3: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
4: methanol
5: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
6: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme
113886-46-7

((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran-4-yl)-(2,4-dinitro-phenyl)-amine

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
2: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
3: methanol
4: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
5: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme
41624-06-0

(3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ol

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 25 percent HBr / CHCl3 / 5 °C
2: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
3: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
4: methanol
5: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
6: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme

((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-(2,4-dinitro-phenyl)-amine

34493-98-6

dibecacin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 6 N aq. HCl, AcOH / 90 °C
2: 25 percent HBr / CHCl3 / 5 °C
3: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C
4: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O
5: methanol
6: H2 / 5 percent Pd/C / acetic acid / 1900 Torr
7: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C
View Scheme

DIBEKACIN Chemical Properties

Product Name: Dibekacin (CAS NO.34493-98-6)


Molecular Formula: C18H37N5O8
Molecular Weight: 451.52g/mol
Mol File: 34493-98-6.mol
Einecs: 252-064-6
Appearance: Yellowish powder
Boiling point: 727.7 °C at 760 mmHg
Flash Point: 393.9 °C
Density: 1.46 g/cm3
Surface Tension: 84.5 dyne/cm
Enthalpy of Vaporization: 121.32 kJ/mol
Vapour Pressure: 1.9E-24 mmHg at 25°C
XLogP3-AA: -5.8
H-Bond Donor: 9
H-Bond Acceptor: 13

DIBEKACIN Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 373mg/kg (373mg/kg)   Journal of Pharmacobio-Dynamics. Vol. 4, Pg. 356, 1981.
mouse LD50 intraperitoneal 11960ug/kg (11.96mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
mouse LD50 intravenous 8950ug/kg (8.95mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
mouse LD50 oral 763mg/kg (763mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
mouse LD50 subcutaneous 15980ug/kg (15.98mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
rat LD50 intraperitoneal 16760ug/kg (16.76mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
rat LD50 intravenous 12510ug/kg (12.51mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.
rat LD50 oral > 6950mg/kg (6950mg/kg)   Japanese Journal of Antibiotics. Vol. 26, Pg. 221, 1973.
rat LD50 subcutaneous 23870ug/kg (23.87mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 119, 1975.

DIBEKACIN Consensus Reports

EPA Genetic Toxicology Program.

DIBEKACIN Safety Profile

Poison by intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. An antibacterial agent. When heated to decomposition it emits toxic fumes of NOx.

DIBEKACIN Specification

 Dibekacin ,its CAS NO. is 34493-98-6,the synonyms is (2r,3r,4s,5s,6r)-4-Amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol ; 6-o-(3-Amino-3-deoxy-α-d-glucopyranosyl)-4-o-(2,6-diamino-2,3,4,6-tetradeoxy-α-d-erythro-hexopyranosyl)-2-deoxy-d-streptamine .

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