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

Base Information

Chemical Name:1-C-(hydroxymethyl)-1-deamino-1-nitro-3,2',6',3''-tetrakis-N-(tert-butoxycarbonyl)kanamycin B
CAS No.:132260-16-3
Molecular Formula:C₃₉H₆₉N₅O₂₁
Molecular Weight:943.998
Hs Code.:

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

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

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

There total 9 articles about 1-C-(hydroxymethyl)-1-deamino-1-nitro-3,2',6',3''-tetrakis-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: 81.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 132260-15-2
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

Guidance literature:: With triethylamine; In chloroform; for 0.5h; Heating;
DOI:10.1021/jm00108a037

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 steps

1: dioxane; methanol / 0.5 h / 40 °C

2: 62 percent / H₂ / 10percent Pd/C / methanol; H₂O / 3 h / 2280 Torr

3: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C

4: 81 percent / triethylamine / CHCl₃ / 0.5 h / Heating

With 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; chloroform; water; 1,2-dichloro-ethane;
DOI:10.1021/jm00108a037

Reference yield:

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

Guidance literature:: Multi-step reaction with 5 steps

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

2: dioxane; methanol / 0.5 h / 40 °C

3: 62 percent / H₂ / 10percent Pd/C / methanol; H₂O / 3 h / 2280 Torr

4: 45 percent / 3-chloroperbenzoic acid, 3-tert-butyl-5-methyl-4-hydroxyphenyl sulfide / 1,2-dichloro-ethane / 0.75 h / 90 °C

5: 81 percent / triethylamine / CHCl₃ / 0.5 h / Heating

With 6,6'-di-tert-butyl-4,4'-thiodi-o-cresol; hydrogen; copper diacetate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00108a037