2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

Base Information

Chemical Name:2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A
CAS No.:106996-47-8
Molecular Formula:C₅₀H₆₄N₄O₂₀S₃
Molecular Weight:1137.27
Hs Code.:

Synonyms:2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

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Chemical Property of 2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

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Technology Process of 2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

There total 1 articles about 2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin 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: 90.0%

: 2466-76-4
N-Acetylimidazole

: 76550-53-3
6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A

: 106996-47-8
2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

Guidance literature:: With pyridine; sodium hydrogencarbonate; In water; dimethyl sulfoxide; Ambient temperature;
DOI:10.1016/0008-6215(92)84101-W

Reference yield:

: 106996-47-8
2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

: 100343-09-7
3'-deoxy-3'-fluorokanamycin A

Guidance literature:: Multi-step reaction with 6 steps

1: 88 mg / pyridine / 0.17 h / 0 - 5 °C

2: 88 percent / Zemplen deacetylation

3: 75 percent / NaOMe / methanol / 0.5 h / 45 °C

4: 31 percent / KHF₂ / ethane-1,2-diol / 3.5 h / 150 - 160 °C

5: Na, liquid NH₃ / 1.) -50 deg C, 5 min 2.) MeOH, -50 deg C -> rt

6: Dowex 50W-X₂(H⁽¹⁺⁾form) / H₂O / 0.25 h / 50 °C

With pyridine; potassium hydrogen bifluoride; Dowex 50W-X₂(H⁽¹⁺⁾form); ammonia; sodium methylate; sodium; In methanol; water; ethylene glycol;
DOI:10.1016/0008-6215(92)84101-W

Reference yield:

: 106996-47-8
2',2''-di-O-acetyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosyl-kanamycin A

: C₂₆H₄₅FN₄O₁₂

Guidance literature:: Multi-step reaction with 5 steps

1: 88 mg / pyridine / 0.17 h / 0 - 5 °C

2: 88 percent / Zemplen deacetylation

3: 75 percent / NaOMe / methanol / 0.5 h / 45 °C

4: 31 percent / KHF₂ / ethane-1,2-diol / 3.5 h / 150 - 160 °C

5: Na, liquid NH₃ / 1.) -50 deg C, 5 min 2.) MeOH, -50 deg C -> rt

With pyridine; potassium hydrogen bifluoride; ammonia; sodium methylate; sodium; In methanol; ethylene glycol;
DOI:10.1016/0008-6215(92)84101-W