Isepamicin

Base Information

• Chemical Name: Isepamicin
• CAS No.: 58152-03-7
• Molecular Formula: C22H43 N5 O12
• Molecular Weight: 569.61
• European Community (EC) Number: 261-143-4
• UNII: G7K224460P
• DSSTox Substance ID: DTXSID1048380
• Nikkaji Number: J22.232A
• Wikipedia: Isepamicin
• Wikidata: Q76149945
• NCI Thesaurus Code: C83838
• ChEMBL ID: CHEMBL272080
• Mol file: 58152-03-7.mol

Synonyms:HAPA-B;Isépalline;Isepacin;isepamicin;isepamicin disulfate;isepamicin monosulfate;isepamicin sulfate;N-(S-3-amino-2-hydroxypropionyl)gentamicin;Sch 21420;Sch-21420

Chemical Property of Isepamicin

Chemical Property:

• Refractive Index: 1.7500 (estimate)
• Boiling Point: 926.8°Cat760mmHg
• PKA: 11.01±0.35(Predicted)
• Flash Point: 514.3°C
• PSA: 297.72000
• Density: 1.53g/cm³
• LogP: -4.64170
• XLogP3: -6.9
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 9
• Exact Mass: 569.29082182
• Heavy Atom Count: 39
• Complexity: 817

Purity/Quality:

99% ^*data from raw suppliers

Isepamicin >99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CN)O)O)O)N)NC(=O)C(CN)O)O
• Isomeric SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O
• Recent NIPH Clinical Trials: Investigation of methods for preventing biofilm formation in peritoneal dialysis-related peritonitis
• Description: Isepamicin is a aminoglycoside antibiotic indicated for use in the treatment of urinary and respiratory tract infections. Although it is less potent than most other aminoglycosides, it is also less nephrotoxic. The broad-spectrum activity of isepamicin generally parallels that of amikacin in vitro.
• Uses: Antibacterial (aminoglyco side).

Technology Process of Isepamicin

There total 10 articles about Isepamicin 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: 57.0%

[2-(6-azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-5-(2-benzyloxy-3-benzyloxycarbonylamino-propionylamino)-4-(3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-carbamic acid benzyl ester → isepamicin (58152-03-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2004.11.130

Reference yield:

sisomicin (32385-11-8) → isepamicin (58152-03-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 65 percent / zinc acetate; TEA / tetrahydrofuran

2.1: 80 percent / dicyclohexylcarbodiimide; hydroxybenzotriazole / methanol

3.1: 76 percent / NEt₃ / tetrahydrofuran

4.1: 75 percent / sulfuric acid / methanol

5.1: silver triflate; 4 Angstroem molecular sieves / benzene; dioxane / 12 h / 20 °C

5.2: 52 percent / silver triflate / benzene; dioxane / 5 h / 0 °C

6.1: 57 percent / hydrogen / Pd/C / methanol; tetrahydrofuran

With 4 A molecular sieve; TEA; sulfuric acid; zinc diacetate; hydrogen; silver trifluoromethanesulfonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; benzene;

DOI:10.1016/j.tetlet.2004.11.130

Reference yield:

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride (42869-68-1) → isepamicin (58152-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver triflate; 4 Angstroem molecular sieves / benzene; dioxane / 12 h / 20 °C

1.2: 52 percent / silver triflate / benzene; dioxane / 5 h / 0 °C

2.1: 57 percent / hydrogen / Pd/C / methanol; tetrahydrofuran

With 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; benzene;

DOI:10.1016/j.tetlet.2004.11.130

upstream raw materials:

C₄₆H₆₁O₁₈N₅

3,6'-bis-N-benzyloxycarbonylgentamicin B

sisomicin

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride

Downstream raw materials:

3,6',3''-tri-N-(t-butoxycarbonyl)-3'''-N-(benzyloxycarbonyl)isepamicin

6'-N-benzyloxycarbonyl-3,3'',3'''-tri-N-(t-butoxycarbonyl)-isepamicin

3,3'',3'''-tri-N-(t-butoxycarbonyl)-isepamicin

3,6',3''-tri-N-(t-butoxycarbonyl)-isepamicin

Refernces

• 1、 Doktorov, Konstantin,Tarpanov, Velichko,Mechkarova, Pepa. "New convenient reagents for chemoselective N-alkoxycarbonylation of (S)-isoserine: Application in the isepamicin synthesis". . p. 3709 - 3718. Retrieved 2008/02/10.