Amdoxovir

Base Information

• Chemical Name: Amdoxovir
• CAS No.: 145514-04-1
• Molecular Formula: C₉H₁₂N₆O₃
• Molecular Weight: 252.233
• UNII: 54I81H0M9C
• DSSTox Substance ID: DTXSID801027435
• Nikkaji Number: J531.849A
• Wikipedia: Amdoxovir
• Wikidata: Q460478
• NCI Thesaurus Code: C76927
• Metabolomics Workbench ID: 144543
• ChEMBL ID: CHEMBL458876
• Mol file: 145514-04-1.mol

Synonyms:2,6-diaminopurine dioxolane;4-(2,6-diamino-9H-purin-9-yl)-1,3,-dioxolane-2-methanol;amdoxovir

Chemical Property of Amdoxovir

Chemical Property:

• Vapor Pressure: 3.05E-19mmHg at 25°C
• Boiling Point: 676.8°Cat760mmHg
• Flash Point: 363.1°C
• PSA: 134.33000
• Density: 2.08g/cm³
• LogP: 0.01690
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 252.09708827
• Heavy Atom Count: 18
• Complexity: 308

Purity/Quality:

98%Min ^*data from raw suppliers

AMDOXOVIR 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(O1)CO)N2C=NC3=C(N=C(N=C32)N)N
• Isomeric SMILES: C1[C@@H](O[C@@H](O1)CO)N2C=NC3=C(N=C(N=C32)N)N
• Recent ClinicalTrials: Adding New Drugs for HIV Infected Patients Failing Current Therapy
• Uses: 2,6-diaminopurine dioxolane can be used in the treatment of HIV-1 and hepatitis B infections (reverse transcriptase inhibitor).

Technology Process of Amdoxovir

There total 30 articles about Amdoxovir 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: 95.0%

(-)-β-D-2-amino-6-chloropurine dioxolane (145513-99-1,145514-00-7) → DAPD (145514-04-1,153611-19-9)

Guidance literature:

Reference yield: 93.0%

isobutyric acid 4(R)-(2,6-diamino-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester (838845-03-7) → DAPD (145514-04-1,153611-19-9)

Guidance literature:

With N-butylamine; In methanol; for 4h; Heating;

DOI:10.1081/NCN-200040643

Reference yield: 90.0%

4-methoxybenzoic acid 4(R)-(2,6-diamino-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester (855520-15-9) → DAPD (145514-04-1,153611-19-9)

Guidance literature:

With N-butylamine; In methanol; for 4h; Heating;

DOI:10.1081/NCN-200040643

upstream raw materials:

9-[(2R,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-[1,3]dioxolan-4-yl]-9H-purine-2,6-diamine

isobutyric acid 4(R)-(2,6-diamino-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester

4-methoxybenzoic acid 4(R)-(2,6-diamino-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester

isobutyric acid 4(R)-(2,6-dichloro-purin-9-yl)-[1,3]-dioxolan-2(R)-yl-methyl ester

Downstream raw materials:

(2S)-ethyl 2-(((((2R,4R)-4-(2-amino-6-hydroxy-9H-purin-9-yl)-1,3-dioxolan-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate

Refernces

• 1、 Zhou, Longhu,Coats, Steven J.,Zhang, Hongwang,Shi, Junxing,Bobeck, Drew R.,Schinazi, Raymond F.. "Scaleable processes for the synthesis of (-)-β-d-2,6-diaminopurine dioxolane (Amdoxovir, DAPD) and (-)-β-d-2-aminopurine dioxolane (APD)". experimental part. p. 5738 - 5743. Retrieved 2012/09/08.
• 2、 Sznaidman, Marcos L.,Du, Jinfa,Pesyan, Amir,Cleary, Darryl G.,Hurley, Kevin P.,Waligora, Frank,Almond, Merrick R.. "Synthesis of (-)-DAPD". . p. 1875 - 1887. Retrieved 2007/10/03.