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4696-76-8

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4696-76-8 Usage

Uses

Kanamycin B (cas# 4696-76-8) is a compound useful in organic synthesis.

Antimicrobial activity

A component of the mixture of kanamycins produced by Streptomyces kanamyceticus. It is approximately twice as active as kanamycin A and is twice as toxic. It is not active against amikacin-resistant strains of MRSA. It is poorly active against Ps. aeruginosa. The pharmacokinetics and uses are similar to those of kanamycin. A 0.5% ophthalmic solution has been used to treat gonococcal ophthalmia neonatorum. It is available in Japan.

Safety Profile

Poison by intravenous route.Moderately toxic by intraperitoneal and subcutaneousroutes. When heated to decomposition it emits toxicfumes of NOx.

Check Digit Verification of cas no

The CAS Registry Mumber 4696-76-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,9 and 6 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 4696-76:
(6*4)+(5*6)+(4*9)+(3*6)+(2*7)+(1*6)=128
128 % 10 = 8
So 4696-76-8 is a valid CAS Registry Number.
InChI:InChI=1/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

4696-76-8Synthetic 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

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;
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

4696-76-8Upstream product

4696-76-8Relevant articles and documents

Epiminodeaminodeoxyaminoglycoside antibiotics and intermediates

-

, (2008/06/13)

Deoxyaminoglycoside antibiotics are prepared in a high yield from phosphorylated aminoglycosides by reacting a phosphorylated aminoglycoside (a) with a silylating agent, or (b) successively with (i) a silylating or acylating agent and (ii) a halogenating agent; then subjecting thus obtained intermediate to reduction. Deoxyaminoglycoside antibiotics are useful for treating infections caused by microorganisms which are resistant or non-resistant to the corresponding aminoglycoside antibiotics.

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