4696-76-8

Basic information

• Product Name: Bekanamycin
• Synonyms: d-streptamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(2,6-diamino-2,;kanendomycin;kdm;nebramycinfactor5;nebramycinv;KANAMYCIN B;Kanamycin b (intermediates);(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
• CAS NO: 4696-76-8
• Molecular Formula: C₁₈H₃₇N₅O₁₀
• Molecular Weight: 483.51
• EINECS: 225-170-5
• Product Categories: Pharmaceutical Intermediates;API;Inhibitors
• Mol File: 4696-76-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 178-182° (dec)
• Boiling Point: 580.49°C (rough estimate)
• Flash Point: 442.3°C
• Appearance: /
• Density: 1.3771 (rough estimate)
• Vapor Pressure: 3.43E-30mmHg at 25°C
• Refractive Index: 1.7600 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Aqueous Acid (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Sparingl
• PKA: 13.07±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Bekanamycin(CAS DataBase Reference)
• NIST Chemistry Reference: Bekanamycin(4696-76-8)
• EPA Substance Registry System: Bekanamycin(4696-76-8)

Safety Data

• Hazardous Substances Data: 4696-76-8(Hazardous Substances Data)

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.

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

• 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 
• 1268528-26-2 pentaazidokanamycin B 
• 132260-18-5 1-C-(hydroxymethyl)kanamycin B 
• 132260-18-5 C₁₉H₃₉N₅O₁₁ 
• 132260-23-2 1-C-(hydroxymethyl)-6''-O-<(2,4,6-triisopropylphenyl)sulfonyl>-1,3,2',6',3''-penta-N-BOC-kanamycin B 
• 132260-22-1 C₅₄H₉₁N₅O₂₃S 
• 132260-21-0 C₅₃H₈₉N₅O₂₂S 
• 132260-20-9 C₅₃H₉₁N₅O₂₀S 
• 132260-25-4 1-C-(hydroxymethyl)-6''-deoxy-6''-azido-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 
• 132260-13-0 1-N-<(benzyloxy)carbonyl>-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B 

Relevant articles and documents

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.