3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C

Base Information

• Chemical Name: 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C
• CAS No.: 133036-43-8
• Molecular Formula: C₃₄H₄₇FN₄O₁₂
• Molecular Weight: 722.765
• Mol file: 133036-43-8.mol

Synonyms:

Chemical Property of 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C

There total 6 articles about 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C 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:

3',4'-dideoxykanamycin C (65566-76-9) → 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C (133036-43-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / sodium carbonate / dioxane; H₂O / 2 h / Ambient temperature

2: 95 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 16 h / Ambient temperature

3: 71 percent / (diethylamino)sulfur trifluoride (DAST) / CH₂Cl₂ / 1.5 h / -60 - 20 °C

4: 80percent aq. acetic acid / 1 h / 90 °C

5: hydrogen / palladium black / dioxane; H₂O; acetic acid / 1 h

6: 1) zinc acetate dihydrate / 1) DMSO, room temp., 1 h; 2) DMSO, room temp., 2 h

With diethylamino-sulfur trifluoride; zinc diacetate; hydrogen; sodium carbonate; toluene-4-sulfonic acid; acetic acid; palladium; In 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.63.3583

Reference yield:

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4',6'-trideoxy-6'-fluorokanamycin C (133036-41-6) → 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C (133036-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 80percent aq. acetic acid / 1 h / 90 °C

2: hydrogen / palladium black / dioxane; H₂O; acetic acid / 1 h

3: 1) zinc acetate dihydrate / 1) DMSO, room temp., 1 h; 2) DMSO, room temp., 2 h

With zinc diacetate; hydrogen; acetic acid; palladium; In 1,4-dioxane; water; acetic acid;

DOI:10.1246/bcsj.63.3583

Reference yield:

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin C (133036-39-2) → 3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C (133036-43-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 16 h / Ambient temperature

2: 71 percent / (diethylamino)sulfur trifluoride (DAST) / CH₂Cl₂ / 1.5 h / -60 - 20 °C

3: 80percent aq. acetic acid / 1 h / 90 °C

4: hydrogen / palladium black / dioxane; H₂O; acetic acid / 1 h

5: 1) zinc acetate dihydrate / 1) DMSO, room temp., 1 h; 2) DMSO, room temp., 2 h

With diethylamino-sulfur trifluoride; zinc diacetate; hydrogen; toluene-4-sulfonic acid; acetic acid; palladium; In 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.63.3583

upstream raw materials:

N-(benzyloxycarbonyl)succinimide

3',4',6'-trideoxy-6'-fluorokanamycin C

3',4'-dideoxykanamycin C

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin C

Downstream raw materials:

3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluoro-3''-N-(trifluoroacetyl)kanamycin C

1-N-<(S)-4-amino-2-hydroxybutanoyl>-3',4',6'-trideoxy-6'-fluorokanamycin C

3,2'-bis(N-benzyloxycarbonyl)-1-N-<(S)-4-benzyloxycarbonylamino-2-hydroxybutanoyl>-3',4',6'-trideoxy-6'-fluoro-3''-N-(trifluoroacetyl)kanamycin C