N-[1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide

Base Information

• Chemical Name: N-[1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide
• CAS No.: 110522-75-3
• Molecular Formula: C13H19N3O5
• Molecular Weight: 297.311
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID50401806
• Mol file: 110522-75-3.mol

Synonyms:N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide;ST056931;NiBu-2'-dC;N4-Isobutyryldeoxycytidine;N4-Isobutyryl-2'-deoxycytidine;DTXSID50401806;AKOS024282524;N-[1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide;FT-0770516

Chemical Property of N-[1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide

Chemical Property:

• Refractive Index: 1.641
• PKA: 10.03±0.20(Predicted)
• PSA: 113.68000
• Density: 1.49 g/cm³
• LogP: -0.44850
• Storage Temp.: −20°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 297.13247072
• Heavy Atom Count: 21
• Complexity: 488

Purity/Quality:

98%, ^*data from raw suppliers

Ibu-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)NC1=NC(=O)N(C=C1)C2CC(C(O2)CO)O

Technology Process of N-[1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide

There total 3 articles about N-[1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide 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%

2-Methylpropionic anhydride (97-72-3) + 2'-Deoxycytidine (951-77-9) → N4-isobutyryll-2'-deoxycytidine (110522-75-3)

Guidance literature:

In N,N-dimethyl-formamide;

DOI:10.1080/07328319708006236

Reference yield:

Isobutyric acid (2R,3S,5R)-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester (110522-80-0) → N4-isobutyryll-2'-deoxycytidine (110522-75-3)

Guidance literature:

With pyridine; water; triethylamine;

DOI:10.1016/S0040-4039(00)95646-6

Reference yield:

2'-Deoxycytidine (951-77-9) → N4-isobutyryll-2'-deoxycytidine (110522-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: triethylamine, water, pyridine

With pyridine; water; triethylamine;

DOI:10.1016/S0040-4039(00)95646-6

upstream raw materials:

Isobutyric acid (2R,3S,5R)-5-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-2-isobutyryloxymethyl-tetrahydro-furan-3-yl ester

2-Methylpropionic anhydride

2'-Deoxycytidine

Downstream raw materials:

N⁴-isobutyryl-2'-deoxycytidine-3'-diisopropylaminocyanoethyl phosphoramidite

2'-Deoxycytidine

4-methylamino-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one

N-(1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)isobutyramide

Refernces

• 1、 Vu, Huynh,McCollum, Christie,Jacobson, Karen,Theisen, Pete,Vinayak, Ravi,et al.. "FAST OLIGONUCLEOTIDE DEPROTECTION. PHOSPHORAMIDITE CHEMISTRY FOR DNA SYNTHESIS". . p. 7269 - 7272. Retrieved 2007/10/02.