N4-Benzoyl-2'-fluoro-2'-deoxycytidine

Base Information

• Chemical Name: N4-Benzoyl-2'-fluoro-2'-deoxycytidine
• CAS No.: 146954-76-9
• Molecular Formula: C16H16FN3O5
• Molecular Weight: 349.319
• DSSTox Substance ID: DTXSID001291107
• Mol file: 146954-76-9.mol

Synonyms:146954-76-9;N4-BENZOYL-2'-FLUORO-2'-DEOXYCYTIDINE;N-Benzoyl-2'-deoxy-2'-fluorocytidine;N4-Benzoyl-2/'-deoxy-2/'-fluorocytidine;N-(1-((2R,3R,4R,5R)-3-Fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;N-[1-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;Cytidine, N-benzoyl-2'-deoxy-2'-fluoro-;n4-benzoyl-2'-deoxy-2'-fluorocytidine;SCHEMBL432297;C16H16FN3O5;DTXSID001291107;HG1112;MFCD22373353;AC-32180;AS-49380;CS-0172704;A900357;J-700216;N-Benzoyl-2 inverted exclamation marka-deoxy-2 inverted exclamation marka-fluorocytidine;N-(1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

Chemical Property of N4-Benzoyl-2'-fluoro-2'-deoxycytidine

Chemical Property:

• PKA: 8.52±0.20(Predicted)
• PSA: 113.68000
• Density: 1.56±0.1 g/cm3(Predicted)
• LogP: 0.15730
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 349.10739878
• Heavy Atom Count: 25
• Complexity: 590

Purity/Quality:

98%, ^*data from raw suppliers

N4-Benzoyl-2''-fluoro-2''-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=NC(=O)N(C=C2)C3C(C(C(O3)CO)O)F
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)NC2=NC(=O)N(C=C2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)F

Technology Process of N4-Benzoyl-2'-fluoro-2'-deoxycytidine

There total 10 articles about N4-Benzoyl-2'-fluoro-2'-deoxycytidine 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%

benzoic acid anhydride (93-97-0) + 2'-deoxy-2'-fluorocytidine (10212-20-1) → N4-benzoyl-2-deoxy-2-fluorocytidine (146954-76-9)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃;

Reference yield: 86.8%

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N4-benzoylcytosine (69304-43-4) → N4-benzoyl-2-deoxy-2-fluorocytidine (146954-76-9)

Guidance literature:

1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl]-N⁴-benzoylcytosine; With trifluoromethylsulfonic anhydride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -20 ℃; for 10h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield:

2'-deoxy-2'-fluorocytidine (10212-20-1) → N4-benzoyl-2-deoxy-2-fluorocytidine (146954-76-9)

Guidance literature:

upstream raw materials:

benzoic acid anhydride

2'-deoxy-2'-fluorocytidine

3’,5’-O-acetyl-2’-deoxy-2’-fluorouridine

2'-deoxy-2'-fluorouridine

Downstream raw materials:

N⁴-benzoyl-2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)cytidine 3'-(β-cyanoethyl N,N-diisopropylphosphoramidite)

C₃₀H₃₀FN₃O₆

N⁴-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-fluoro-2'-deoxycytidine