N-benzoylcytidine

Base Information

• Chemical Name: N-benzoylcytidine
• CAS No.: 13089-48-0
• Molecular Formula: C16H17N3O6
• Molecular Weight: 347.327
• Hs Code.: 29349990
• European Community (EC) Number: 603-444-9
• DSSTox Substance ID: DTXSID201316254
• Nikkaji Number: J451.572B
• Mol file: 13089-48-0.mol

Synonyms:N-benzoylcytidine;13089-48-0;N4-Benzoylcytidine;Cytidine, N-benzoyl-;N4-Benzoyl-L-cytidine;N-[1-[(2R,3R,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;MFCD00010572;N-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;1018812-31-1;4-n-benzoyl cytidine;N4-Benzoylcytidine, 99%;SCHEMBL565904;AMY3711;BNXBRFDWSPXODM-BPGGGUHBSA-N;DTXSID201316254;N-(1-(3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;AKOS015839054;AKOS015895282;CS-15645;CS-0008585;F12710;J-700223

Chemical Property of N-benzoylcytidine

Chemical Property:

• Appearance/Colour: slightly pink solid
• Melting Point: 230-234 °C (dec.)(lit.)
• Refractive Index: 46 ° (C=1, DMSO)
• PKA: 8.61±0.20(Predicted)
• PSA: 133.91000
• Density: 1.59 g/cm³
• LogP: -0.81990
• Storage Temp.: Store at 0°C
• Solubility.: Soluble in 1N NaOH at 10mg/ml. Also soluble in methanol or DMSO
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 347.11173527
• Heavy Atom Count: 25
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

N4-Benzoylcytidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=NC(=O)N(C=C2)C3C(C(C(O3)CO)O)O
• 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)O
• Uses: N4-Benzoylcytidine is a useful building block for oligoribonucleotide synthesis N-Benzoylcytidine is a useful building block for oligoribonucleotide synthesis.

Technology Process of N-benzoylcytidine

There total 18 articles about N-benzoylcytidine 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%

O2',O3',O5'-tris-trimethylsilyl-N4-benzoylcytidine (118684-37-0) → N4-benzoylcytidine (13089-48-0)

Guidance literature:

With water; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 0.0166667h; Further Variations:; Reagents; Product distribution;

DOI:10.1081/SCC-120017200

Reference yield: 99.0%

2'-O-(4-methoxybenzyl)-N4-benzoylcytidine (80015-59-4) → N4-benzoylcytidine (13089-48-0)

Guidance literature:

With trityl tetrafluoroborate; In nitromethane; water; for 1.5h; Ambient temperature;

DOI:10.1021/jo00175a010

Reference yield: 98.3%

benzoic acid anhydride (93-97-0) + CYTIDINE (65-46-3) → N4-benzoylcytidine (13089-48-0)

Guidance literature:

In N,N-dimethyl-formamide; for 0.0166667h; Irradiation;

DOI:10.1016/S0040-4039(97)01684-5

upstream raw materials:

2'-O-(4-methoxybenzyl)-N⁴-benzoylcytidine

4-N-benzoyl-2',3'-O-isopropylidenecytidine

benzoyl chloride

CYTIDINE

Downstream raw materials:

N⁴-benzoyl-2',3'-O-(triphenylphosphoranediyl)-O²,5'-cyclocytidine

1-(2'-O,3'-O-Cyclopentyl-5'-hydroxy-β-D-erythro-pentofuranosyl)-N⁴-benzoylcytosine

4-N-benzoyl-1-(5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)cytosine

(5'R)-N⁴-benzoyl-1-[5'-O-(tert-butyldimethylsilyl)-2'-deoxy-3'-C,5'-C-[(5'-C,6'-C-methano)ethano]-α-D-ribofuranosyl]cytosine

Refernces

• 1、 Antczak, Nicole M.,Arnold, Jamie J.,Caldwell, Haley S.,Cameron, Craig E.,Ciota, Alexander T.,Harki, Daniel A.,Jose, Joyce,Narayanan, Anoop,Ngo, Kiet A.,Passow, Kellan T.,Sturla, Shana J.. "A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide". . p. 15429 - 15439. Retrieved 2021/11/12.
• 2、 Vohtancev, Ivan P.,Sherstyuk, Yuliya V.,Silnikov, Vladimir N.,Abramova, Tatyana V.. "Effective Synthesis of 5-Iodo Derivatives of Pyrimidine Morpholino Nucleosides". . p. 332 - 342. Retrieved 2018/05/29.