4696-76-8

Usage

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

Synthetic route

di-tert-butyl dicarbonate (24424-99-5) + kananmycin B (4696-76-8) → 1,3,2',6',3''-penta-N-tert-butoxycarbonyl kanamycin B

Conditions	Yield
With sodium carbonate In water; isopropyl alcohol at 30℃; for 6h; Temperature;	94%

p-toluenesulfonyl chloride (98-59-9) + kananmycin B (4696-76-8) → 1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin B (60929-91-1, 119818-17-6)

Conditions	Yield
With sodium carbonate In ethanol; dichloromethane; water at 25℃; for 16h; Reagent/catalyst; Solvent; Temperature;	92.3%

di-tert-butyl dicarbonate (24424-99-5) + kananmycin B (4696-76-8) → 1,3,2',6',3''-penta-N-BOC-kanamycin B (64271-30-3)

Conditions	Yield
In water; dimethyl sulfoxide at 60℃; for 6h;	90%

acetone O-<(vinyloxy)carbonyl>oxime (139705-38-7) + kananmycin B (4696-76-8) → C33H47N5O20

Conditions	Yield
In phosphate buffer at 0℃; for 5h; pH=8.0;	84%

kananmycin B (4696-76-8) + 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine (207857-15-6) → guanidinoboc10-kanamycin B

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃;	80%

kananmycin B (4696-76-8) → pentaazidokanamycin B (1268528-26-2)

Conditions	Yield
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) + kananmycin B (4696-76-8) → 3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B (132260-09-4)

Conditions	Yield
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) + 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine (207857-15-6) → C73H127N15O30 (320616-55-5)

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃; for 72h;	65%

acetic anhydride (108-24-7) + kananmycin B (4696-76-8) → penta-N-hexa-O-acetylkanamycin B (144727-28-6)

Conditions	Yield
With pyridine

toluene-4-sulfonic acid (104-15-4) + kananmycin B (4696-76-8) → 1,3,2',6',3''-penta-N-p-toluenesulfonylkanamycin B (60929-91-1, 119818-17-6)

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

benzyl chloroformate (501-53-1) + kananmycin B (4696-76-8) → 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)

Conditions	Yield
With sodium carbonate In water Yield given;

kananmycin B (4696-76-8) + ATP (56-65-5) → C28H49N10O16P

Conditions	Yield
at 37℃; aminoglycoside-4'-nucleotidyltransferaze of Bacillus brevis, MgCl2, potassium phosphate buffer (pH 6.0);

kananmycin B (4696-76-8) → 2-deoxystreptamine (2037-48-1) + kanosamine (60183-25-7) + 2,6-dideoxy-2,6-diamino-D-glucose (59433-00-0)

Conditions	Yield
With hydrogenchloride for 0.5h; Product distribution; Heating; other aminoglycosides and their carbenicillin products;

kananmycin B (4696-76-8) → 4'',6''-O-cyclohexylidenekanamycin B (64879-71-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 2 h / Ambient temperature 2: dimethylformamide / Ambient temperature View Scheme

kananmycin B (4696-76-8) → C61H97N5O22S (132260-19-6)

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

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

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

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

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

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

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

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

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

Conditions	Yield
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) → C44H80N6O20 (132260-27-6)

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

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

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

Conditions	Yield
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

Downstream Products

• 132260-09-4 3,2',6'-tris-N-(tert-butoxycarbonyl)kanamycin B 
• 64271-30-3 1,3,2',6',3''-penta-N-BOC-kanamycin B 
• 144727-28-6 penta-N-hexa-O-acetylkanamycin B 
• 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 
• 2037-48-1 2-deoxystreptamine 
• 60183-25-7 kanosamine 
• 59433-00-0 2,6-dideoxy-2,6-diamino-D-glucose 
• 1268528-26-2 pentaazidokanamycin B 
• 31077-70-0 3''-deamino-3''-hydroxy-kanamycin B 
• 60929-91-1 kanamycin B 1,3,2',6',3''-penta-p-toluenesulfonate 
• 3847-27-6 Kanamycin A sulfate 

Relevant academic research and scientific papers

Epiminodeaminodeoxyaminoglycoside antibiotics and intermediates

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.