3'-Deoxy-3'-fluorokanamycin A

Base Information

• Chemical Name: 3'-Deoxy-3'-fluorokanamycin A
• CAS No.: 100343-09-7
• Molecular Formula: C18H35 F N4 O10
• Molecular Weight: 486.495
• DSSTox Substance ID: DTXSID60905421
• Mol file: 100343-09-7.mol

Synonyms:3'-deoxy-3'-fluorokanamycin A

Chemical Property of 3'-Deoxy-3'-fluorokanamycin A

Chemical Property:

• Boiling Point: 807.1°Cat760mmHg
• Flash Point: 441.9°C
• PSA: 262.38000
• Density: 1.59g/cm³
• LogP: -3.51300
• XLogP3: -5.9
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 486.23372149
• Heavy Atom Count: 33
• Complexity: 643

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)F)O)O)OC3C(C(C(C(O3)CO)O)N)O)N

Technology Process of 3'-Deoxy-3'-fluorokanamycin A

There total 9 articles about 3'-Deoxy-3'-fluorokanamycin 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:

3',4'-anhydro-6'-N-(benzyloxycarbonyl)-4'-epi-1,3,3''-tri-N-tosylkanamycin A (144218-67-7) → 6-O-[(3-deoxy-3-amino)-α-D-glucopyranosyl]-2-deoxy-streptamine (20744-51-8,236401-43-7) + 4'-deoxy-4'-fluorokanamycin A carbonate + 3'-deoxy-3',4'-diepi-3'-fluorokanamycin A (100343-09-7)

Guidance literature:

With potassium hydrogen bifluoride; ammonia; sodium; Yield given. Multistep reaction. Yields of byproduct given; 1) ethane-1,2-diol, 150 deg C , 6 h, 2) -60 deg C, 2 min;

DOI:10.1016/S0008-6215(00)90996-0

Reference yield:

C26H45FN4O12 → 3'-deoxy-3'-fluorokanamycin A (100343-09-7)

Guidance literature:

With Dowex 50W-X₂(H⁽¹⁺⁾form); In water; at 50 ℃; for 0.25h; Yield given;

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'-fluorokanamycin A (100343-09-7)

Guidance literature:

Multi-step reaction with 7 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

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

7: 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; sodium hydrogencarbonate; In methanol; water; ethylene glycol; dimethyl sulfoxide;

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

upstream raw materials:

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

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

Refernces

• 1、 Takahashi, Yoshiaki,Tsuneda, Sayori,Tsuchiya, Tsutomu,Koyama, Yoshiko,Umezawa, Sumio. "Synthesis of 4'-deoxy-4'-fluorokanamycin A and B". . p. 89 - 106. Retrieved 2007/10/02.