Acetic acid 3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid 3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 87190-76-9
• Molecular Formula: C13H14N8O4
• Molecular Weight: 346.305
• NSC Number: 382316
• ChEMBL ID: CHEMBL368650

Synonyms:CHEMBL368650;NSC382316;BDBM50056853;NSC-382316;Acetic acid 3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Acetic acid 3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 346.11380096
• Heavy Atom Count: 25
• Complexity: 658

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(CC(O1)N2C=CC(=NC2=O)N3C=NC=N3)N=[N+]=[N-]

Technology Process of Acetic acid 3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

There total 1 articles about Acetic acid 3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 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: 62.0%

1,2,4-Triazole (288-88-0) + 3'-azido-2',3'-dideoxy-5'-O-acetyluridine (84472-87-7) → Acetic acid (2S,3S,5R)-3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (87190-76-9)

Guidance literature:

With pyridine; 4-chlorophenylphosphorodichloridate; for 72h; Ambient temperature;

DOI:10.1021/jm00366a006

Reference yield: 86.0%

Acetic acid (2S,3S,5R)-3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (87190-76-9) → 3'-azido-2',3'-dideoxycytidine (84472-89-9)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; for 4h; Ambient temperature;

DOI:10.1021/jm00366a006

Reference yield:

Acetic acid (2S,3S,5R)-3-azido-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (87190-76-9) → 3'-amino-2',3'-dideoxycytidine (84472-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / aq. NH₄OH / dioxane / 4 h / Ambient temperature

2: 65 percent / H₂ / 10percent Pd/C / ethanol / 5 h / 2585.7 Torr

With ammonium hydroxide; hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol;

DOI:10.1021/jm00366a006

upstream raw materials:

1,2,4-Triazole

3'-azido-2',3'-dideoxy-5'-O-acetyluridine

Downstream raw materials:

3'-azido-2',3'-dideoxycytidine

3'-amino-2',3'-dideoxycytidine

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