Oxaunomycin

Base Information

• Chemical Name: Oxaunomycin
• CAS No.: 105615-58-5
• Molecular Formula: C₂₆H₂₉NO₁₀
• Molecular Weight: 515.517
• UNII: AJ227FR53I
• DSSTox Substance ID: DTXSID70909632
• Nikkaji Number: J35.093A
• Wikidata: Q82879275
• Mol file: 105615-58-5.mol

Synonyms:10-epi-oxaunomycin;oxaunomycin

Chemical Property of Oxaunomycin

Chemical Property:

• Vapor Pressure: 7.81E-20mmHg at 25°C
• Boiling Point: 687.3°Cat760mmHg
• Flash Point: 369.5°C
• PSA: 200.00000
• Density: 1.63g/cm³
• LogP: 1.73810
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 515.17914612
• Heavy Atom Count: 37
• Complexity: 903

Purity/Quality:

OXAUNOMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC(C2=C(C1O)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)OC5CC(C(C(O5)C)O)N)O
• Isomeric SMILES: CC[C@]1(C[C@@H](C2=C([C@H]1O)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N)O

Technology Process of Oxaunomycin

There total 4 articles about Oxaunomycin 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%

13-deoxocarminomycin (76034-18-9) → oxaunomycin (105615-58-5,103782-06-5)

Guidance literature:

With trimethylamine-N-oxide; In N,N-dimethyl-formamide; for 40h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80527-X

Reference yield:

D788-1 → oxaunomycin (105615-58-5,103782-06-5) + 10-epi-Oxaunomycin (103782-06-5)

Guidance literature:

With citrate buffer; iodine; In acetone; at 25 - 30 ℃; for 5h; Yield given. Yields of byproduct given; Irradiation;

DOI:10.7164/antibiotics.48.1153

Reference yield:

10-O-acetyl-3'-N-trifluoroacetyloxaunomycin (141085-71-4) → oxaunomycin (105615-58-5,103782-06-5)

Guidance literature:

With sodium hydroxide; at 40 ℃; for 1h;

DOI:10.1248/cpb.40.61

upstream raw materials:

13-deoxocarminomycin

10-O-acetyl-3'-N-trifluoroacetyloxaunomycin

10-O-acetyl-4'-O-p-nitrobenzoyl-3'-N-trifluoroacetyloxaunomycin

Refernces

• 1、 Kita,Maeda,Kirahara,Fujii,Nakajima,Yamamoto,Tamura,Fujioka. "Synthesis of a potent rhodomycin, oxaunomycin, and its analogs". . p. 61 - 65. Retrieved 2007/10/02.