3',4'-dideoxy-3',4'-didehydro kanamycin B
dibecacin
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide In water | 98% |
With platinum(IV) oxide; hydrogen; acetic acid In water at 20℃; for 24h; Temperature; | 96% |
penta-N-acetyldibekacin
dibecacin
Conditions | Yield |
---|---|
With hydrazine hydrate at 100℃; for 72h; | 70% |
O-3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranosyl-(1->6)-1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1a
dibecacin
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -80℃; for 0.75h; | 1% |
dibecacin
Conditions | Yield |
---|---|
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 |
dibecacin
Conditions | Yield |
---|---|
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 |
{(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
dibecacin
Conditions | Yield |
---|---|
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 |
dibecacin
Conditions | Yield |
---|---|
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 |
((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-bromo-tetrahydro-pyran-4-yl)-(2,4-dinitro-phenyl)-amine
dibecacin
Conditions | Yield |
---|---|
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 |
(3R,4S,5S,6R)-3,5-Bis-benzyloxy-6-benzyloxymethyl-4-(2,4-dinitro-phenylamino)-tetrahydro-pyran-2-ol
dibecacin
Conditions | Yield |
---|---|
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 |
dibecacin
Conditions | Yield |
---|---|
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 |
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: NaOAc 2: 56 percent / NaBH4 / aq. ethanol / 0.5 h / 5 °C 3: H2 / Raney Ni (T-4) / 760 Torr 4: Na2CO3 / H2O; dioxane 5: 80 percent aq. AcOH / 60 °C 6: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C 7: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O 8: methanol 9: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 10: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C View Scheme |
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: methanol 2: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 3: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C View Scheme |
Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 56 percent / NaBH4 / aq. ethanol / 0.5 h / 5 °C 2: H2 / Raney Ni (T-4) / 760 Torr 3: Na2CO3 / H2O; dioxane 4: 80 percent aq. AcOH / 60 °C 5: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C 6: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O 7: methanol 8: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 9: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C View Scheme |
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 2: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C View Scheme |
C56H71N7O19
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O 2: methanol 3: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 4: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C View Scheme |
[(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,4R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: d-10-camphorsulfonic acid / dimethylformamide 2: NaOAc 3: 56 percent / NaBH4 / aq. ethanol / 0.5 h / 5 °C 4: H2 / Raney Ni (T-4) / 760 Torr 5: Na2CO3 / H2O; dioxane 6: 80 percent aq. AcOH / 60 °C 7: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C 8: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O 9: methanol 10: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 11: 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-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-2,2-dimethyl-7-nitro-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: H2 / Raney Ni (T-4) / 760 Torr 2: Na2CO3 / H2O; dioxane 3: 80 percent aq. AcOH / 60 °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 |
methyl-β-kanopyranosaminide
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: Na2CO3 / H2O; acetone 2: BaO, Ba(OH)2*8H2O / dimethylformamide 3: 6 N aq. HCl, AcOH / 90 °C 4: 25 percent HBr / CHCl3 / 5 °C 5: 77 percent / AgClO4, sym-collidine / benzene; dioxane / 0.5 h / 24 °C 6: 1.) Dowex 1*2(OH- form); 2.) Ba(OH)2*8H2O / 1.) acetone, H2O; 2.) dioxane, H2O 7: methanol 8: H2 / 5 percent Pd/C / acetic acid / 1900 Torr 9: 70 percent / 80 percent aq. NH2NH2 / 72 h / 100 °C View Scheme |
3-acetamido-2,4,6-tri-O-benzyl-3-deoxy-α-D-glucopyranosyl chloride
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3.7 g / silver toluene-p-sulphonate / benzene; CH2Cl2 / 1.) 40 deg C, 24 h, 2.) 25 deg C, 72 h 2: 1 percent / ammonia, sodium / tetrahydrofuran / 0.75 h / -80 °C View Scheme |
(1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)tetrahydropyran-2-yl]oxy-cyclohexane-1,2-diol
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / aq. sodium hydrogencarbonate / methanol / 25 °C 2: 3.7 g / silver toluene-p-sulphonate / benzene; CH2Cl2 / 1.) 40 deg C, 24 h, 2.) 25 deg C, 72 h 3: 1 percent / ammonia, sodium / tetrahydrofuran / 0.75 h / -80 °C View Scheme |
1,3,2',6'-tetrakis-N-benzyloxycarbonylgentamine C1a
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3.7 g / silver toluene-p-sulphonate / benzene; CH2Cl2 / 1.) 40 deg C, 24 h, 2.) 25 deg C, 72 h 2: 1 percent / ammonia, sodium / tetrahydrofuran / 0.75 h / -80 °C View Scheme |
1,3,2',6',3''-penta-N-benzylsulfonyl-2''-O-benzylsulfonyl-3',4'-dideoxykanamycin B-3'-ene
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 84 percent / sodium, ethanol / liquid ammonia / 0.67 h / -60 - -55 °C 2: 98 percent / hydrogen / platinum oxide / H2O View Scheme |
1,3,2',6',3''-penta-N-benzylsulfonyl-2''-O-benzylsulfonyl-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin B-3'-ene
dibecacin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 600 mg / acetic acid / 0.5 h / 90 °C 2: 84 percent / sodium, ethanol / liquid ammonia / 0.67 h / -60 - -55 °C 3: 98 percent / hydrogen / platinum oxide / H2O View Scheme |
dibecacin
di-tert-butyl dicarbonate
3',4'-dideoxy-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)kanamycin B
Conditions | Yield |
---|---|
With triethylamine In water at 60℃; for 0.666667h; | 96% |
With triethylamine In 1,4-dioxane at 60℃; for 1.5h; | 90% |
dibecacin
benzyl chloroformate
1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin B
Conditions | Yield |
---|---|
With sodium carbonate In water; acetone | 92% |
chloro-trimethyl-silane
dibecacin
Conditions | Yield |
---|---|
With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 90℃; for 16h; Temperature; Time; | 73% |
dibecacin
Conditions | Yield |
---|---|
With pyruvate kinase; recombinant Enterococcus faecium aminoglycoside 2''-phosphotransferase type IIa N196D/D268N mutant; potassium chloride; phosphoenolpyruvate trianion; ATP; NADH; magnesium chloride; lactate dehydrogenase pH=7.5; Kinetics; Reagent/catalyst; aq. HEPES buffer; Enzymatic reaction; |
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
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. |
EPA Genetic Toxicology Program.
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 ,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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