N4-benzoyl-2',3'-dideoxycytidine

Base Information

• Chemical Name: N4-benzoyl-2',3'-dideoxycytidine
• CAS No.: 120885-60-1
• Molecular Formula: C16H17N3O4
• Molecular Weight: 315.329
• DSSTox Substance ID: DTXSID70350423
• Wikidata: Q82126363
• ChEMBL ID: CHEMBL1736922
• Mol file: 120885-60-1.mol

Synonyms:N4-benzoyl-2',3'-dideoxycytidine;120885-60-1;MLS000851174;N-[1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide;SMR000457417;cid_678696;SCHEMBL3485953;CHEMBL1736922;BDBM87459;DTXSID70350423;HMS1661L06;HMS2776P05;CCG-55777;AKOS024325904;SR-01000644784-1;N-[1-[(2R,5S)-5-(hydroxymethyl)-2-oxolanyl]-2-oxo-4-pyrimidinyl]benzamide;N-[1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-2-oxidanylidene-pyrimidin-4-yl]benzamide;N-[2-keto-1-[(2R,5S)-5-methyloltetrahydrofuran-2-yl]pyrimidin-4-yl]benzamide;N-(1-((2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide;N-{1-[(2R,5S)-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl}benzamide

Chemical Property of N4-benzoyl-2',3'-dideoxycytidine

Chemical Property:

• PSA: 96.94000
• Density: 1.41g/cm3
• LogP: 0.99970
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 315.12190603
• Heavy Atom Count: 23
• Complexity: 525

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1CO)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3
• Isomeric SMILES: C1C[C@@H](O[C@@H]1CO)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3

Technology Process of N4-benzoyl-2',3'-dideoxycytidine

There total 9 articles about N4-benzoyl-2',3'-dideoxycytidine 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: 98.0%

benzoic acid anhydride (93-97-0) + 2`,3`-dideoxycytidine (7481-89-2) → N4-benzoyl-2',3'-dideoxycytidine (120885-60-1)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2017.01.038

Reference yield: 90.0%

N4-benzoyl-2',3'-dideoxy-5'-O-tritylcytidine (127073-28-3) → N4-benzoyl-2',3'-dideoxycytidine (120885-60-1)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 10 - 15 ℃; for 0.5h;

DOI:10.1002/jhet.5570260605

Reference yield: 65.4%

benzoyl chloride (98-88-4) + 2`,3`-dideoxycytidine (7481-89-2) → N4-benzoyl-2',3'-dideoxycytidine (120885-60-1)

Guidance literature:

2`,3`-dideoxycytidine; With pyridine; chloro-trimethyl-silane; at 20 ℃; Inert atmosphere; Sonication;

benzoyl chloride; at 20 ℃; for 2h; Inert atmosphere;

With ammonium hydroxide; In water; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.7b11623

upstream raw materials:

N⁴-benzoyl-2',3'-dideoxy-5'-O-tritylcytidine

benzoic acid anhydride

N⁴-benzoyl-2',3'-dideoxy-3'-iodo-5'-O-tritylcytidine

N⁴-benzoyl-2'-deoxy-3'-O-mesyl-5'-O-tritylcytidine

Refernces

• 1、 Tam, Chun Pong,Zhou, Lijun,Fahrenbach, Albert C.,Zhang, Wen,Walton, Travis,Szostak, Jack W.. "Synthesis of a Nonhydrolyzable Nucleotide Phosphoroimidazolide Analogue That Catalyzes Nonenzymatic RNA Primer Extension". . p. 783 - 792. Retrieved 2018.