3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

Base Information

Chemical Name:3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A
CAS No.:76550-60-2
Molecular Formula:C₅₃H₆₈N₄O₂₀S₃
Molecular Weight:1177.34
Hs Code.:

Synonyms:3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

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Chemical Property of 3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

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Technology Process of 3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

There total 6 articles about 3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin 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: 80.0%

: 108-24-7
acetic anhydride

: 76550-54-4
6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

: 76550-60-2
3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

Guidance literature:: With pyridine; Ambient temperature;
DOI:10.1016/S0008-6215(00)85232-5

Reference yield:

: kanamycin A monocarbonate monohydrate

: 76550-60-2
3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / zinc acetate dihydrate / dimethylsulfoxide / 1 h / Ambient temperature

2: 98 percent / anhydrous sodium carbonate / H₂O; dioxane / Ambient temperature

3: 98 percent / p-toluenesulfonic acid / dimethylformamide / Ambient temperature

4: 90 percent / 50 percent NaH / dimethylformamide / 1.) 1 h, 2.) overnight, RT

5: 40 percent / 0.08 percent HCl, 5 Angstroem molecular sieve / CH₂Cl₂; tetrahydrofuran / 0.28 h / Heating

6: 80 percent / pyridine / Ambient temperature

With pyridine; hydrogenchloride; 5A molecular sieve; zinc diacetate; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)85232-5

Reference yield:

: 76550-51-1
6'-N-(benzyloxyarbonyl)-1,3,3''-tri-N-tosylkanamycin A

: 76550-60-2
3',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-5,2'-O-isopropylidene-1,3,3''-tri-N-tosylkanamycin A

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / p-toluenesulfonic acid / dimethylformamide / Ambient temperature

2: 90 percent / 50 percent NaH / dimethylformamide / 1.) 1 h, 2.) overnight, RT

3: 40 percent / 0.08 percent HCl, 5 Angstroem molecular sieve / CH₂Cl₂; tetrahydrofuran / 0.28 h / Heating

4: 80 percent / pyridine / Ambient temperature

With pyridine; hydrogenchloride; 5A molecular sieve; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)85232-5