4-Amino-1-(4-C-azido-2',3',5'-tri-O-(2-methylpropanoyl)-beta-D-ribofuranosyl)pyrimidin-2(1H)-one

Base Information

• Chemical Name: 4-Amino-1-(4-C-azido-2',3',5'-tri-O-(2-methylpropanoyl)-beta-D-ribofuranosyl)pyrimidin-2(1H)-one
• CAS No.: 690270-29-2
• Molecular Formula: C21H30N6O8
• Molecular Weight: 494.4983
• NCI Thesaurus Code: C87439
• Mol file: 690270-29-2.mol

Synonyms:balapiravir;R 1626;R-1626;R1626

Chemical Property of 4-Amino-1-(4-C-azido-2',3',5'-tri-O-(2-methylpropanoyl)-beta-D-ribofuranosyl)pyrimidin-2(1H)-one

Chemical Property:

• PSA: 198.79000
• LogP: 1.72966
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 494.21251194
• Heavy Atom Count: 35
• Complexity: 971

Purity/Quality:

97% ^*data from raw suppliers

Balapiravir >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)OCC1(C(C(C(O1)N2C=CC(=NC2=O)N)OC(=O)C(C)C)OC(=O)C(C)C)N=[N+]=[N-]
• Isomeric SMILES: CC(C)C(=O)OC[C@@]1([C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)OC(=O)C(C)C)OC(=O)C(C)C)N=[N+]=[N-]
• Uses: Balapiravir is used as nanocontainers for transporting nonpolar, lipophilic substances such as antibiotics.

Technology Process of 4-Amino-1-(4-C-azido-2',3',5'-tri-O-(2-methylpropanoyl)-beta-D-ribofuranosyl)pyrimidin-2(1H)-one

There total 4 articles about 4-Amino-1-(4-C-azido-2',3',5'-tri-O-(2-methylpropanoyl)-beta-D-ribofuranosyl)pyrimidin-2(1H)-one 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: 89.0%

2-Methylpropionic anhydride (97-72-3) + 4'-azidocytidine (478182-28-4) → balapiravir (690270-29-2)

Guidance literature:

With dmap; potassium hydroxide; In tetrahydrofuran; water; at 10 - 15 ℃; pH=8 - 11; Product distribution / selectivity;

Reference yield: 85.3%

4'-azidocytidine (478182-28-4) + isobutyryl chloride (79-30-1) → balapiravir (690270-29-2)

Guidance literature:

With dmap; potassium hydroxide; In tetrahydrofuran; water; at 5 ℃; pH=~ 8.5; Product distribution / selectivity;

Reference yield:

4'-azidocytidine (478182-28-4) + isobutyric Acid (79-31-2) → balapiravir (690270-29-2)

Guidance literature:

With dmap; sodium hydroxide; sodium hydrogencarbonate; 1,1'-carbonyldiimidazole; In tetrahydrofuran; water; at 20 ℃; pH=~ 9 - 9.5; Product distribution / selectivity;

upstream raw materials:

4'-azidocytidine

isobutyric Acid

2-Methylpropionic anhydride

isobutyryl chloride

Refernces

• 1、 -. "ANTIVIRAL NUCLEOSIDE DERIVATIVES". Page 35. . Retrieved 2010/02/07.