3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A

Base Information

• Chemical Name: 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A
• CAS No.: 139978-77-1
• Molecular Formula: C₄₇H₆₃FN₄O₁₈S₃
• Molecular Weight: 1087.23
• Mol file: 139978-77-1.mol

Synonyms:3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A

Chemical Property of 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A

There total 5 articles about 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-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: 16.0%

2',3'-anhydro-4'',6''-O-cyclohexylidene-3'-epi-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A (105507-34-4) → 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A (139978-77-1) + 2'-deoxy-2',3'-diepi-2'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A (139978-78-2)

Guidance literature:

With potassium hydrogen bifluoride; In ethylene glycol; at 150 - 160 ℃; for 3.5h;

DOI:10.1016/0008-6215(92)84101-W

Reference yield:

6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A (76550-53-3) → 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A (139978-77-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine, 5percent NaHCO₃ / dimethylsulfoxide; H₂O / Ambient temperature

2: 88 mg / pyridine / 0.17 h / 0 - 5 °C

3: 88 percent / Zemplen deacetylation

4: 75 percent / NaOMe / methanol / 0.5 h / 45 °C

5: 31 percent / KHF₂ / ethane-1,2-diol / 3.5 h / 150 - 160 °C

With pyridine; potassium hydrogen bifluoride; sodium methylate; sodium hydrogencarbonate; In methanol; water; ethylene glycol; dimethyl sulfoxide;

DOI:10.1016/0008-6215(92)84101-W

Reference yield:

2',2''-di-O-acetyl-3'-O-benzylsulfonyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A (107009-76-7) → 3'-deoxy-3'-fluoro-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A (139978-77-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Zemplen deacetylation

2: 75 percent / NaOMe / methanol / 0.5 h / 45 °C

3: 31 percent / KHF₂ / ethane-1,2-diol / 3.5 h / 150 - 160 °C

With potassium hydrogen bifluoride; sodium methylate; In methanol; ethylene glycol;

DOI:10.1016/0008-6215(92)84101-W

upstream raw materials:

2',3'-anhydro-4'',6''-O-cyclohexylidene-3'-epi-6'-N-methoxycarbonyl-1,3,3''-tri-N-tosylkanamycin A

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

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

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

Downstream raw materials:

3'-deoxy-3'-fluorokanamycin A