Bredinin 5'-monophosphate

Base Information

• Chemical Name: Bredinin 5'-monophosphate
• CAS No.: 62025-48-3
• Molecular Formula: C₉H₁₄N₃O₉P
• Molecular Weight: 339.199
• DSSTox Substance ID: DTXSID40977565
• Nikkaji Number: J647.734H
• Wikidata: Q76009794
• ChEMBL ID: CHEMBL1794685
• Mol file: 62025-48-3.mol

Synonyms:4-carbamoyl-1-beta-D-ribofuranosylimidazolium-5-olate;Brd-MP;bredinin 5'-monophosphate

Chemical Property of Bredinin 5'-monophosphate

Chemical Property:

• Vapor Pressure: 1.5E-32mmHg at 25°C
• Boiling Point: 872.7°C at 760 mmHg
• Flash Point: 481.6°C
• PSA: 207.40000
• Density: 2.3g/cm³
• LogP: -1.88360
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 339.04676603
• Heavy Atom Count: 22
• Complexity: 473

Purity/Quality:

97% ^*data from raw suppliers

Mizoribine5''-Monophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)O)C(=O)N
• Isomeric SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)O)C(=O)N
• Uses: Mizoribine 5''-Monophosphate, is a derivative of Mizoribine (M385500), which is a nucleoside antibiotic with cytotoxic and immunosuppressive activity. Mizoribine 5''-Monophosphate, also selectively inhibits the activities of mammalian DNA polymerases in vitro.

Technology Process of Bredinin 5'-monophosphate

There total 7 articles about Bredinin 5'-monophosphate 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:

5'-O-(3-Oxo-2,4,3-benzodioxaphosphepan-3-yl)bredinin (174498-84-1) → mizoribine 5'-monophosphate (62025-48-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/0040-4039(95)02110-8

Reference yield:

Mizoribine<*> (50924-49-7) → mizoribine 5'-monophosphate (62025-48-3)

Guidance literature:

Multi-step reaction with 7 steps

1: TsOH / Ambient temperature

2: 71 percent / aq. acetic acid / Ambient temperature; Irradiation

3: 78 percent / Et₃N / dimethylformamide / Ambient temperature

4: 1.) tetrazole; 2.) I₂ / 1.) CH₂Cl₂; 2.) H₂O, r.t.

5: 90percent TFA / Ambient temperature

6: dimethylformamide / 90 °C

7: H₂ / Pd-C / methanol

With 1H-tetrazole; hydrogen; iodine; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)02110-8

Reference yield:

2-Amino-N-(2,3-O-isopropylidene-β-D-ribofuranosyl)malonamide (99592-66-2) → mizoribine 5'-monophosphate (62025-48-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / Et₃N / dimethylformamide / Ambient temperature

2: 1.) tetrazole; 2.) I₂ / 1.) CH₂Cl₂; 2.) H₂O, r.t.

3: 90percent TFA / Ambient temperature

4: dimethylformamide / 90 °C

5: H₂ / Pd-C / methanol

With 1H-tetrazole; hydrogen; iodine; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)02110-8

upstream raw materials:

5'-O-(3-Oxo-2,4,3-benzodioxaphosphepan-3-yl)bredinin

Mizoribine^<*>

2-Amino-N-(2,3-O-isopropylidene-β-D-ribofuranosyl)malonamide

2-(tert-Butoxycarbonylamino)-N-(2,3-O-isopropylidene-β-D-ribofuranosyl)malonamide

Refernces