1-(2-Azido-2-deoxyarabinofuranosyl)thymine

Base Information

• Chemical Name: 1-(2-Azido-2-deoxyarabinofuranosyl)thymine
• CAS No.: 131232-94-5
• Molecular Formula: C₁₀H₁₃N₅O₅
• Molecular Weight: 283.244
• DSSTox Substance ID: DTXSID80156973
• Wikidata: Q83025097
• Mol file: 131232-94-5.mol

Synonyms:1-(2-azido-2-deoxy-beta-D-arabinofuranosyl)thymine;1-(2-azido-2-deoxyarabinofuranosyl)thymine;1-ADAT

Chemical Property of 1-(2-Azido-2-deoxyarabinofuranosyl)thymine

Chemical Property:

• Melting Point: 172.5-174 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 154.56000
• Density: g/cm³
• LogP: -1.36044
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 283.09166853
• Heavy Atom Count: 20
• Complexity: 514

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C(C(C(O2)CO)O)N=[N+]=[N-]
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)N=[N+]=[N-]

Technology Process of 1-(2-Azido-2-deoxyarabinofuranosyl)thymine

There total 4 articles about 1-(2-Azido-2-deoxyarabinofuranosyl)thymine 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: 100.0%

1-(2-azido-2-deoxy-3,5-O-TIPDS-β-D-arabinofuranosyl)thymine (131132-32-6) → 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)thymine (131232-94-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jm00107a018

Reference yield:

N3-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyl disiloxane-1,3-diyl)5-methyluridine (131132-30-4) → 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)thymine (131232-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / diethyl azodicarboxylate, triphenyl phosphorazidate, triphenylphosphine / tetrahydrofuran / 4 h / Ambient temperature

2: 90 percent / concd. NH₄OH / methanol / 2 h / Ambient temperature

3: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 2 h / Ambient temperature

With ammonium hydroxide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00107a018

Reference yield:

N3-benzoyl-1-(2-azido-2-deoxy-3,5-O-TIPDS-β-D-arabinofuranosyl)thymine (131132-31-5) → 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)thymine (131232-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / concd. NH₄OH / methanol / 2 h / Ambient temperature

2: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 2 h / Ambient temperature

With ammonium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1021/jm00107a018

upstream raw materials:

1-(2-azido-2-deoxy-3,5-O-TIPDS-β-D-arabinofuranosyl)thymine

N³-benzoyl-3′,5′-O-(1,1,3,3-tetraisopropyl disiloxane-1,3-diyl)5-methyluridine

N³-benzoyl-1-(2-azido-2-deoxy-3,5-O-TIPDS-β-D-arabinofuranosyl)thymine

1-[(6aR,8R,9S,9aR)-tetrahydro-9-hydroxy-2,2,4,4-tetraisopropyl-6H-furo[3,2-f]-[1,3,5,2,4]trioxadisilocin-8-yl](5-methylpyrimidine)-2.4(1H_.3H)-dione

Refernces