Tecadenoson

Base Information

• Chemical Name: Tecadenoson
• CAS No.: 204512-90-3
• Molecular Formula: C₁₄H₁₉N₅O₅
• Molecular Weight: 337.335
• UNII: GZ1X96601Z
• DSSTox Substance ID: DTXSID80174415
• Nikkaji Number: J1.055.589B
• Wikidata: Q27088953
• NCI Thesaurus Code: C77980
• Pharos Ligand ID: XWZBB8BNXVCH
• Metabolomics Workbench ID: 149353
• ChEMBL ID: CHEMBL392149
• Mol file: 204512-90-3.mol

Synonyms:CVT 510;CVT-510;N-(3-tetrahydrofuranyl)-6-aminopurine riboside;tecadenoson

Chemical Property of Tecadenoson

Chemical Property:

• Vapor Pressure: 7.4E-21mmHg at 25°C
• Boiling Point: 704.9°C at 760 mmHg
• Flash Point: 380.1°C
• Density: 1.89g/cm³
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 337.13861872
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1COCC1NC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO)O)O
• Isomeric SMILES: C1COC[C@@H]1NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
• Recent ClinicalTrials: Safety Study of Tecadenoson to Treat Atrial Fibrillation

Technology Process of Tecadenoson

There total 3 articles about Tecadenoson 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: 67.9%

6-Chloropurine riboside (2004-06-0) + (R)-3-aminotetrahydrofuranyl tosylate (111769-27-8,104530-80-5) → Tecadenoson (204512-90-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tert-butyl alcohol; at 83 ℃; for 27h;

DOI:10.1016/j.bmcl.2007.10.028

Reference yield:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester (309724-86-5) → Tecadenoson (204512-90-3)

Guidance literature:

With ammonia; In methanol;

DOI:10.1016/j.bmcl.2003.09.094

Reference yield:

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) → Tecadenoson (204512-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / ethanol / Heating

2: NH₃ / methanol

With ammonia; triethylamine; In methanol; ethanol;

DOI:10.1016/j.bmcl.2003.09.094

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-[(R)-(tetrahydro-furan-3-yl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester

6-Chloropurine riboside

(R)-3-aminotetrahydrofuranyl tosylate

2',3',5'-O-triacetyl-6-chloroinosine