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

Base Information

Chemical Name:1-C-(hydroxymethyl)-6''-deoxy-6''-acetamido-1,3,2',6',3''-pentakis-N-(tert-butoxycarbonyl)kanamycin B
CAS No.:132260-26-5
Molecular Formula:C₄₆H₈₂N₆O₂₁
Molecular Weight:1055.18
Hs Code.:

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

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

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

There total 12 articles about 1-C-(hydroxymethyl)-6''-deoxy-6''-acetamido-1,3,2',6',3''-pentakis-N-(tert-butoxycarbonyl)kanamycin B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 9 steps

1: dioxane; methanol / 0.5 h / 40 °C

2: 65 percent / pyridine / 64 h

3: 76 percent / H₂ / 10percent Pd/C / methanol / 2280 Torr

4: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating

5: 72 percent / triethylamine / CHCl₃ / 1.5 h / Heating

6: 1.) H₂, (BOC)2O / 1.) Raney nickel W₂ / 1.) methanol, 4 atm, 4 h, 2.) 20 h

7: 95 percent / LiN₃ / dimethylformamide / 23 h / 65 °C

8: 1.) triphenylphosphine, 2.) 33percent aqueous NH₃ / 1.) pyridine, RT, 2 h, 2.) 24 h

9: 73 percent / ethanol / 1.5 h / Ambient temperature

With pyridine; ammonium hydroxide; lithium azide; di-tert-butyl dicarbonate; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; Raney nickel W₂; In 1,4-dioxane; methanol; ethanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00108a037

Reference yield:

: 132260-09-4
3,2',6'-tris-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

Guidance literature:: Multi-step reaction with 10 steps

1: 73 percent / copper(II) acetate monohydrate / dimethylformamide / 1.5 h

2: dioxane; methanol / 0.5 h / 40 °C

3: 65 percent / pyridine / 64 h

4: 76 percent / H₂ / 10percent Pd/C / methanol / 2280 Torr

5: 40 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.5 h / Heating

6: 72 percent / triethylamine / CHCl₃ / 1.5 h / Heating

7: 1.) H₂, (BOC)2O / 1.) Raney nickel W₂ / 1.) methanol, 4 atm, 4 h, 2.) 20 h

8: 95 percent / LiN₃ / dimethylformamide / 23 h / 65 °C

9: 1.) triphenylphosphine, 2.) 33percent aqueous NH₃ / 1.) pyridine, RT, 2 h, 2.) 24 h

10: 73 percent / ethanol / 1.5 h / Ambient temperature

With pyridine; ammonium hydroxide; lithium azide; di-tert-butyl dicarbonate; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; hydrogen; copper diacetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; Raney nickel W₂; In 1,4-dioxane; methanol; ethanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00108a037

Reference yield:

: 4696-76-8
kananmycin B

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

Guidance literature:: 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

With pyridine; ammonium hydroxide; lithium azide; di-tert-butyl dicarbonate; 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; zinc diacetate; hydrogen; copper diacetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; Raney nickel W₂; In 1,4-dioxane; methanol; ethanol; chloroform; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00108a037