2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

Base Information

• Chemical Name: 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B
• CAS No.: 144487-82-1
• Molecular Formula: C₆₁H₇₇N₅O₂₀S₅
• Molecular Weight: 1360.63

Synonyms:2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

Chemical Property of 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

Chemical Property:

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Technology Process of 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

There total 3 articles about 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin 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: 89.0%

N-Acetylimidazole (2466-76-4) + 4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B (78788-44-0,119818-20-1) → 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B (144487-82-1)

Guidance literature:

With pyridine; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/0008-6215(92)80060-E

Reference yield:

cycloxexanone dimethyl ketal (933-40-4) → 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B (144487-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / 50 °C

2: 89 percent / pyridine / dimethylsulfoxide / Ambient temperature

With pyridine; toluene-4-sulfonic acid; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80060-E

Reference yield:

3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B (119783-92-5) → 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B (144487-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / p-toluenesulfonic acid / dimethylformamide / 2 h / 50 °C

2: 89 percent / pyridine / dimethylsulfoxide / Ambient temperature

With pyridine; toluene-4-sulfonic acid; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80060-E

upstream raw materials:

N-Acetylimidazole

4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

cycloxexanone dimethyl ketal

3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B

Downstream raw materials:

2''-O-acetyl-5-O-benzoyl-4'',6''-O-cyclohexylidene-3'-deoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B

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