4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A

Base Information

• Chemical Name: 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A
• CAS No.: 80860-35-1
• Molecular Formula: C₄₄H₇₆N₄O₁₉
• Molecular Weight: 965.103
• Mol file: 80860-35-1.mol

Synonyms:4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A

Chemical Property of 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A

There total 2 articles about 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A 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: 83.0%

cycloxexanone dimethyl ketal (933-40-4) + di-tert-butyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,4S,5S,6R)-6-(((tert-butoxycarbonyl)amino)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate (80860-34-0) → 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A (80860-35-1)

Guidance literature:

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

DOI:10.1248/cpb.29.3464

Reference yield:

kanamycin A (59-01-8) → 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A (80860-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / 25percent triethylamine / dioxane; H₂O / 24 h / Ambient temperature

2: 83 percent / p-toluenesulfonic acid / dimethylformamide / Ambient temperature

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

DOI:10.1248/cpb.29.3464

Reference yield: 75.0%

benzoyl chloride (98-88-4) + 4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A (80860-35-1) → 2',3',2''-tri-O-benzoyl-4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A (80860-36-2)

Guidance literature:

With pyridine; at 5 ℃;

DOI:10.1248/cpb.29.3464

upstream raw materials:

cycloxexanone dimethyl ketal

di-tert-butyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,4S,5S,6R)-6-(((tert-butoxycarbonyl)amino)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

kanamycin A

Downstream raw materials:

2',3',2''-tri-O-benzoyl-4'',6''-O-cyclohexylidene-tetra-N-tert-butoxycarbonylkanamycin A

3',4'-dideoxykanamycin A

3',4'-dideoxy-3'-enekanamycin A

2',3',2''-tri-O-benzoyl-4'',6''-O-cyclohexylidene-4'-methylsulfonyl-tetra-N-tert-butoxycarbonylkanamycin A