Trabodenoson

Base Information

• Chemical Name: Trabodenoson
• CAS No.: 871108-05-3
• Molecular Formula: C₁₅H₂₀N₆O₆
• Molecular Weight: 380.36
• UNII: 1T237110W4
• ChEMBL ID: CHEMBL3545407
• DSSTox Substance ID: DTXSID90236139
• Metabolomics Workbench ID: 153988
• NCI Thesaurus Code: C152705
• Wikidata: Q27252846
• Mol file: 871108-05-3.mol

Synonyms:trabodenoson

Chemical Property of Trabodenoson

Chemical Property:

• Boiling Point: 691.2±65.0 °C(Predicted)
• PKA: 12.99±0.70(Predicted)
• Density: 1.87±0.1 g/cm3(Predicted)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 380.14443238
• Heavy Atom Count: 27
• Complexity: 531

Purity/Quality:

97% ^*data from raw suppliers

Trabodenoson 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)C4C(C(C(O4)CO[N+](=O)[O-])O)O
• Isomeric SMILES: C1CCC(C1)NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO[N+](=O)[O-])O)O
• Recent ClinicalTrials: A Phase II Study to Evaluate the Additivity of Trabodenoson to Latanoprost in Adults With Ocular Hypertension or Primary Open-Angle Glaucoma
• Uses: Trabodenoson alters ECM turnover by TM cells and increases conventional outflow facility, which accounts for its ability to lower IOP in young and aged mice.

Technology Process of Trabodenoson

There total 7 articles about Trabodenoson 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:

2′,3′-O-isopropylidene-N6-cyclopentyladenosine-5′-nitrate (871108-04-2) → ((2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate (871108-05-3)

Guidance literature:

2′,3′-O-isopropylidene-N⁶-cyclopentyladenosine-5′-nitrate; With water; trifluoroacetic acid; at 20 ℃; for 0.5h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

Cyclopentamine (1003-03-8) → ((2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate (871108-05-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethanol / 2 h / Reflux

2.1: toluene-4-sulfonic acid / acetone / 1.5 h / 40 °C

2.2: pH 8

3.1: nitric acid; acetic anhydride / dichloromethane / 0.83 h / -23 - -15 °C

3.2: pH 7

4.1: trifluoroacetic acid; water / 0.5 h / 2 °C

4.2: 10 °C

With water; nitric acid; acetic anhydride; toluene-4-sulfonic acid; trifluoroacetic acid; In ethanol; dichloromethane; acetone;

Reference yield:

N-cyclopentyladenosine (41552-82-3) → ((2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate (871108-05-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / acetone / 1.5 h / 40 °C

1.2: pH 8

2.1: nitric acid; acetic anhydride / dichloromethane / 0.83 h / -23 - -15 °C

2.2: pH 7

3.1: trifluoroacetic acid; water / 0.5 h / 2 °C

3.2: 10 °C

With water; nitric acid; acetic anhydride; toluene-4-sulfonic acid; trifluoroacetic acid; In dichloromethane; acetone;

upstream raw materials:

2′,3′-O-isopropylidene-N⁶-cyclopentyladenosine-5′-nitrate

6-Chloropurine riboside

Cyclopentamine

N-cyclopentyladenosine