5-Trifluoromethyl-2'-deoxycytidine

Base Information

• Chemical Name: 5-Trifluoromethyl-2'-deoxycytidine
• CAS No.: 66384-66-5
• Molecular Formula: C10H12F3N3O4
• Molecular Weight: 295.218
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60216605
• Nikkaji Number: J588.002E
• Wikidata: Q83092850
• ChEMBL ID: CHEMBL3220081
• Mol file: 66384-66-5.mol

Synonyms:2'-deoxy-5-trifluoromethylcytidine;5-trifluoromethyl-2'-deoxycytidine;TFMDC

Chemical Property of 5-Trifluoromethyl-2'-deoxycytidine

Chemical Property:

• Melting Point: 121 °C
• Boiling Point: 433 °C at 760 mmHg
• Flash Point: 215.7 °C
• PSA: 110.60000
• Density: 1.82 g/cm³
• LogP: 0.06620
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 295.07799036
• Heavy Atom Count: 20
• Complexity: 477

Purity/Quality:

99% ^*data from raw suppliers

5-(TRIFLUOROMETHYL)-2'-DEOXYCYTIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)C(F)(F)F)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=NC2=O)N)C(F)(F)F)CO)O

Technology Process of 5-Trifluoromethyl-2'-deoxycytidine

There total 9 articles about 5-Trifluoromethyl-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: 96.7%

C24H18Cl2F3N3O6 → 5-Trifluoromethyl-2'-deoxycytidine (66384-66-5)

Guidance literature:

With methanol; sodium methylate; at -15 - -5 ℃; for 4h; Reagent/catalyst; Temperature;

Reference yield: 73.0%

sodium triflate (2926-30-9) + 2'-Deoxycytidine (951-77-9) → 5-Trifluoromethyl-2'-deoxycytidine (66384-66-5)

Guidance literature:

With tert.-butylhydroperoxide; In water; at 0 - 20 ℃; for 3h;

DOI:10.1039/c3md00159h

Reference yield: 69.0%

3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxycytidine (76514-04-0) → 5-Trifluoromethyl-2'-deoxycytidine (66384-66-5)

Guidance literature:

With ammonia; at 5 ℃;

DOI:10.1039/P19800002755

upstream raw materials:

3',5'-di-O-acetyl-5-(trifluoromethyl)-2'-deoxycytidine

5-iodo-4-acetamido-(2'-deoxy-3'-acetoxy-5'-acetoxymethyl)cytidine

N⁴-acetyl-1-<2'-deoxy-3',5'-di-O-acetyl-β-D-ribofyranosyl>cytosine

sodium triflate

Downstream raw materials:

Benzoic acid (2R,3S,5R)-5-(4-amino-2-oxo-5-trifluoromethyl-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester

Refernces

• 1、 Ito, Yuta,Matsuo, Misaki,Osawa, Takashi,Hari, Yoshiyuki. "Triplex- and duplex-forming abilities of oligonucleotides containing 2′-deoxy-5-trifluoromethyluridine and 2′-deoxy-5-trifluoromethylcytidine". . p. 982 - 988. Retrieved 2018/11/10.
• 2、 Kobayashi, Yoshiro,Yamamoto, Kenjiro,Asai, Toyohira,Nakano, Masanori,Kumadaki, Itsumaro. "Studies on Organic Fluorine Compounds. Part 35. Trifluoromethylation of Pyrimidine- and Purine-nucleosides with Trifluoromethyl-Copper Complex". . p. 2755 - 2761. Retrieved 2007/10/02.