Fortimicin B

Base Information

• Chemical Name: Fortimicin B
• CAS No.: 54783-95-8
• Molecular Formula: C₁₅H₃₂N₄O₅
• Molecular Weight: 348.443
• UNII: 50PN6JXE5M
• DSSTox Substance ID: DTXSID7022625
• Nikkaji Number: J34.181I
• Wikidata: Q27155224
• Metabolomics Workbench ID: 143726
• Mol file: 54783-95-8.mol

Synonyms:fortimicin B

Chemical Property of Fortimicin B

Chemical Property:

• Vapor Pressure: 1.54E-13mmHg at 25°C
• Melting Point: 101-103°
• Boiling Point: 532°C at 760 mmHg
• PKA: 13.45±0.70(Predicted)
• Flash Point: 275.5°C
• PSA: 158.24000
• Density: 1.26g/cm³
• LogP: -0.29130
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 348.23727013
• Heavy Atom Count: 24
• Complexity: 404

Purity/Quality:

95% ^*data from raw suppliers

FORTIMICIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC(C(O1)OC2C(C(C(C(C2O)NC)OC)O)N)N)N
• Isomeric SMILES: C[C@@H]([C@@H]1CC[C@H]([C@H](O1)O[C@@H]2[C@H]([C@@H]([C@@H]([C@H]([C@H]2O)NC)OC)O)N)N)N

Technology Process of Fortimicin B

There total 54 articles about Fortimicin B 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: 82.0%

2-epi-fortimicin B 1,2;4,5-biscarbamate dihydrochloride (76801-49-5,80408-10-2) → 2-epi-fortimicin B (54783-95-8,71658-12-3,71772-09-3,72843-38-0,73173-66-7,73285-05-9,76822-41-8,78821-54-2,79703-14-3,122517-24-2)

Guidance literature:

With sodium hydroxide; at 75 ℃; for 66h;

DOI:10.1016/S0008-6215(00)80392-4

Reference yield: 74.0%

1,2',6'-tri-N-acetyl-2-epi-fortimicin B 4,5-carbamate (76801-55-3,76822-44-1) → 2-epi-fortimicin B (54783-95-8,71658-12-3,71772-09-3,72843-38-0,73173-66-7,73285-05-9,76822-41-8,78821-54-2,79703-14-3,122517-24-2)

Guidance literature:

With sodium hydroxide; at 95 ℃; for 48h;

DOI:10.1016/S0008-6215(00)80392-4

Reference yield: 61.8%

fortimicin A sulfate (66768-12-5,72275-67-3,73285-04-8,78781-03-0,78853-70-0,82731-19-9) → fortimicin B (54783-95-8,71658-12-3,71772-09-3,72843-38-0,73173-66-7,73285-05-9,76822-41-8,78821-54-2,79703-14-3,122517-24-2) + 2'-N-glycylfortimicin B (71241-90-2)

Guidance literature:

With sodium hydroxide; In water; for 4h; Heating;

DOI:10.1016/S0008-6215(00)85995-9

upstream raw materials:

1,2-di-N-benzyloxycarbonyl-6'-epi-fortimicin B-4,5-carbamate

1,2'-di-N-benzyloxycarbonyl-6'-iminofortimicin B-4,5-carbamate

1,2'-di-N-benzyloxycarbonyl-6'-N-chlorofortimicin B-4,5-carbamate

1,2'-di-N-benzyloxycarbonyl-6'-N-(2,2,2-trichloroethoxycarbonyl)-fortimicin B-4,5-carbamate

Downstream raw materials:

1,2',6'-tri-N-benzyloxycarbonyl-6'-epi-fortimicin B

6'-epi-fortimicin A disulfate

1,2',6',2-tetra-N-benzyloxycarbonyl-6'-epi-fortimicin B

6'-epi-fortimicin A

Refernces

2-SUBSTITUTED FORTIMICINS BY RING OPENING OF 2-DEOXY-1,2-EPIMINO-2-EPI-FORTIMICIN B AND BY NUCLEOPHILIC DISPLACEMENTS OF 2-O-(METHYLSULFONYL)FORTIMICIN DERIVATIVES

10.1016/S0008-6215(00)81869-8

The research aimed to synthesize and evaluate 2-substituted fortimicins, a class of aminocyclitol antibiotics, through the ring-opening of 2-deoxy-1,2-epimino-2-epi-fortimicin B and nucleophilic displacements of 2-O-(methylsulfonyl)fortimicin derivatives. The study concluded that the stereochemistry of the azide displacements with different Zmethanesulfonates had a conformational basis, and several 2-substituted fortimicins were prepared and tested for antibacterial activity. Key chemicals used in the process included chloride, azide, cyanide, N-dimethylformamide, and various fortimicin derivatives, as well as reagents like Girard’s reagent T and N-(N-benzyloxycarbonylglycyloxy)succinimide.