Product Name

  • Name

    Bekanamycin

  • EINECS 225-170-5
  • CAS No. 4696-76-8
  • Article Data2
  • CAS DataBase
  • Density 1.59g/cm3
  • Solubility
  • 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
  • Appearance
  • Safety Poison by intravenous route. Moderately toxic by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 4696-76-8 (Bekanamycin)
  • Hazard Symbols
  • Synonyms KanamycinB (7CI,8CI); 2'-Amino-2'-deoxykanamycin; Aminodeoxykanamycin; Bekanamycin; KDM;Kanendomycin; NK 1006; Nebramycin V; Nebramycin factor 5
  • PSA 288.40000
  • LogP -3.82350

Synthetic route

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

kananmycin B
4696-76-8

kananmycin B

1,3,2',6',3''-penta-N-tert-butoxycarbonyl kanamycin 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%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

kananmycin B
4696-76-8

kananmycin B

1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin 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%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

kananmycin B
4696-76-8

kananmycin B

1,3,2',6',3''-penta-N-BOC-kanamycin 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%
acetone O-<(vinyloxy)carbonyl>oxime
139705-38-7

acetone O-<(vinyloxy)carbonyl>oxime

kananmycin B
4696-76-8

kananmycin B

C33H47N5O20

C33H47N5O20

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

kananmycin B

1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine
207857-15-6

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

guanidinoboc10-kanamycin B

guanidinoboc10-kanamycin B

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

kananmycin B

pentaazidokanamycin 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
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

kananmycin B
4696-76-8

kananmycin B

3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin 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;
kananmycin B
4696-76-8

kananmycin B

1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine
207857-15-6

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

C73H127N15O30
320616-55-5

C73H127N15O30

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

acetic anhydride

kananmycin B
4696-76-8

kananmycin B

penta-N-hexa-O-acetylkanamycin B
144727-28-6

penta-N-hexa-O-acetylkanamycin B

Conditions
ConditionsYield
With pyridine
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

kananmycin B
4696-76-8

kananmycin B

1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin 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;
benzyl chloroformate
501-53-1

benzyl chloroformate

kananmycin B
4696-76-8

kananmycin B

N,N'-bis-benzyloxycarbonyl-O4-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O6-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine
65269-36-5

N,N'-bis-benzyloxycarbonyl-O4-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O6-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine

Conditions
ConditionsYield
With sodium carbonate In water Yield given;
kananmycin B
4696-76-8

kananmycin B

ATP
56-65-5

ATP

C28H49N10O16P

C28H49N10O16P

Conditions
ConditionsYield
at 37℃; aminoglycoside-4'-nucleotidyltransferaze of Bacillus brevis, MgCl2, potassium phosphate buffer (pH 6.0);
kananmycin B
4696-76-8

kananmycin B

A

2-deoxystreptamine
2037-48-1

2-deoxystreptamine

B

kanosamine
60183-25-7

kanosamine

C

2,6-dideoxy-2,6-diamino-D-glucose
59433-00-0

2,6-dideoxy-2,6-diamino-D-glucose

Conditions
ConditionsYield
With hydrogenchloride for 0.5h; Product distribution; Heating; other aminoglycosides and their carbenicillin products;
...Expand
kananmycin B
4696-76-8

kananmycin B

4'',6''-O-cyclohexylidenekanamycin B
64879-71-6

4'',6''-O-cyclohexylidenekanamycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide / 2 h / Ambient temperature
2: dimethylformamide / Ambient temperature
View Scheme
kananmycin B
4696-76-8

kananmycin B

C61H97N5O22S
132260-19-6

C61H97N5O22S

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
View Scheme
Multi-step reaction with 6 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-6''-deoxy-6''-chlorokanamycin B
132260-28-7

1-C-(hydroxymethyl)-6''-deoxy-6''-chlorokanamycin B

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
5: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
6: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
7: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
8: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
9: 88.5 percent / lithium chloride / dimethylformamide / 7 h / 90 °C
10: CF3COOH / Ambient temperature
View Scheme
Multi-step reaction with 12 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
7: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
8: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
9: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
10: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
11: 88.5 percent / lithium chloride / dimethylformamide / 7 h / 90 °C
12: CF3COOH / Ambient temperature
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-6''-deoxy-6''-acetamidokanamycin B
132297-01-9

1-C-(hydroxymethyl)-6''-deoxy-6''-acetamidokanamycin B

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
5: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
6: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
7: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
8: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
9: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
10: 1.) triphenylphosphine, 2.) 33percent aqueous NH3 / 1.) pyridine, RT, 2 h, 2.) 24 h
11: 73 percent / ethanol / 1.5 h / Ambient temperature
12: CF3COOH / Ambient temperature
View Scheme
Multi-step reaction with 14 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
7: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
8: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
9: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
10: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
11: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
12: 1.) triphenylphosphine, 2.) 33percent aqueous NH3 / 1.) pyridine, RT, 2 h, 2.) 24 h
13: 73 percent / ethanol / 1.5 h / Ambient temperature
14: CF3COOH / Ambient temperature
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-6''-deoxy-6''-azidokanamycin B
132297-00-8

1-C-(hydroxymethyl)-6''-deoxy-6''-azidokanamycin B

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
5: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
6: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
7: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
8: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
9: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
10: CF3COOH / Ambient temperature
View Scheme
Multi-step reaction with 12 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
7: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
8: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
9: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
10: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
11: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
12: CF3COOH / Ambient temperature
View Scheme
kananmycin B
4696-76-8

kananmycin B

3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B
132260-14-1

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
View Scheme
Multi-step reaction with 6 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
View Scheme
kananmycin B
4696-76-8

kananmycin B

3,2',6'-tris-N-(tert-butoxycarbonyl)-3''-N-(trifluoroacetyl)kanamycin B
132260-10-7

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1.1: zinc(II) acetate dihydrate / dimethyl sulfoxide / 21 °C
1.2: 5 h / 21 °C
2.1: dimethyl sulfoxide / 5 h / 21 °C
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B
132260-17-4

1-C-(hydroxymethyl)-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
5: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C
6: 81 percent / triethylamine / CHCl3 / 0.5 h / Heating
7: 80.5 percent / hydrogen / Raney nickel W2 catalyst / methanol / 3 h / 3040 Torr
View Scheme
Multi-step reaction with 9 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
7: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C
8: 81 percent / triethylamine / CHCl3 / 0.5 h / Heating
9: 80.5 percent / hydrogen / Raney nickel W2 catalyst / methanol / 3 h / 3040 Torr
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-N-<(benzyloxy)carbonyl>-3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B
132260-12-9

1-N-<(benzyloxy)carbonyl>-3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
View Scheme
Multi-step reaction with 4 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-deamino-1-nitro-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B
132260-15-2

1-deamino-1-nitro-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
5: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
7: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-1-deamino-1-nitro-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B
132260-16-3

1-C-(hydroxymethyl)-1-deamino-1-nitro-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
5: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C
6: 81 percent / triethylamine / CHCl3 / 0.5 h / Heating
View Scheme
Multi-step reaction with 8 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 62 percent / H2 / 10percent Pd/C / methanol; H2O / 3 h / 2280 Torr
7: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C
8: 81 percent / triethylamine / CHCl3 / 0.5 h / Heating
View Scheme
kananmycin B
4696-76-8

kananmycin B

C44H80N6O20
132260-27-6

C44H80N6O20

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
5: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
6: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
7: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
8: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
9: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
10: 1.) triphenylphosphine, 2.) 33percent aqueous NH3 / 1.) pyridine, RT, 2 h, 2.) 24 h
View Scheme
Multi-step reaction with 12 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
7: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
8: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
9: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
10: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
11: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
12: 1.) triphenylphosphine, 2.) 33percent aqueous NH3 / 1.) pyridine, RT, 2 h, 2.) 24 h
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-6''-deoxy-6''-chloro-1,3,2',6',3''-pentakis-N-(tert-butoxycarbonyl)kanamycin B
132260-24-3

1-C-(hydroxymethyl)-6''-deoxy-6''-chloro-1,3,2',6',3''-pentakis-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
5: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
6: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
7: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
8: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
9: 88.5 percent / lithium chloride / dimethylformamide / 7 h / 90 °C
View Scheme
Multi-step reaction with 11 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
7: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
8: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
9: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
10: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
11: 88.5 percent / lithium chloride / dimethylformamide / 7 h / 90 °C
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-N-<(benzyloxy)carbonyl>-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B
132260-13-0

1-N-<(benzyloxy)carbonyl>-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
View Scheme
Multi-step reaction with 5 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
View Scheme
kananmycin B
4696-76-8

kananmycin B

1-C-(hydroxymethyl)-6''-deoxy-6''-acetamido-1,3,2',6',3''-pentakis-N-(tert-butoxycarbonyl)kanamycin B
132260-26-5

1-C-(hydroxymethyl)-6''-deoxy-6''-acetamido-1,3,2',6',3''-pentakis-N-(tert-butoxycarbonyl)kanamycin B

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h
3: dioxane; methanol / 0.5 h / 40 °C
4: 65 percent / pyridine / 64 h
5: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
6: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
7: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
8: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
9: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
10: 1.) triphenylphosphine, 2.) 33percent aqueous NH3 / 1.) pyridine, RT, 2 h, 2.) 24 h
11: 73 percent / ethanol / 1.5 h / Ambient temperature
View Scheme
Multi-step reaction with 13 steps
1: 1.) Zn(OAc)2*2H2O / 1.) DMSO, RT, overnight, 2.) 5 h
2: 98 percent / dimethylsulfoxide / 1.5 h / Ambient temperature
3: 79 percent / dimethylformamide / 15 h / Ambient temperature
4: 33percent aqueous NH3 / tetrahydrofuran / 39 h / Ambient temperature
5: dioxane; methanol / 0.5 h / 40 °C
6: 65 percent / pyridine / 64 h
7: 76 percent / H2 / 10percent Pd/C / methanol / 2280 Torr
8: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating
9: 72 percent / triethylamine / CHCl3 / 1.5 h / Heating
10: 1.) H2, (BOC)2O / 1.) Raney nickel W2 / 1.) methanol, 4 atm, 4 h, 2.) 20 h
11: 95 percent / LiN3 / dimethylformamide / 23 h / 65 °C
12: 1.) triphenylphosphine, 2.) 33percent aqueous NH3 / 1.) pyridine, RT, 2 h, 2.) 24 h
13: 73 percent / ethanol / 1.5 h / Ambient temperature
View Scheme

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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