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

Base Information

• Chemical Name: 1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C
• CAS No.: 133036-40-5
• Molecular Formula: C₅₆H₆₈N₄O₁₇
• Molecular Weight: 1069.17

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

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

Chemical Property:

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

There total 3 articles about 1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin 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: 95.0%

cycloxexanone dimethyl ketal (933-40-4) + 1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin C (133036-39-2) → 1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C (133036-40-5)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1246/bcsj.63.3583

Reference yield:

3',4'-dideoxykanamycin C (65566-76-9) → 1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C (133036-40-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.63.3583

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C (133036-40-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.63.3583

upstream raw materials:

cycloxexanone dimethyl ketal

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

3',4'-dideoxykanamycin C

benzyl chloroformate

Downstream raw materials:

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

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

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

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

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