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

Base Information

• Chemical Name: 3',4',6'-trideoxy-6'-fluorokanamycin C
• CAS No.: 133036-42-7
• Molecular Formula: C₁₈H₃₅FN₄O₈
• Molecular Weight: 454.496
• Mol file: 133036-42-7.mol

Synonyms:

Chemical Property of 3',4',6'-trideoxy-6'-fluorokanamycin C

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3',4',6'-trideoxy-6'-fluorokanamycin C

There total 4 articles about 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',4',6'-trideoxy-6'-fluorokanamycin C (133036-42-7)

Guidance literature:

Multi-step reaction with 5 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

With diethylamino-sulfur trifluoride; 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',4',6'-trideoxy-6'-fluorokanamycin C (133036-42-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 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',4',6'-trideoxy-6'-fluorokanamycin C (133036-42-7)

Guidance literature:

Multi-step reaction with 4 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

With diethylamino-sulfur trifluoride; 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:

3',4'-dideoxykanamycin C

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

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4',6'-trideoxy-6'-fluorokanamycin C

1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C

Downstream raw materials:

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

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

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

3,2',6'-tris(N-benzyloxycarbonyl)-3',4'-dideoxy-6'-C-(fluoromethyl)kanamycin B

Refernces