Raluridine

Base Information

• Chemical Name: Raluridine
• CAS No.: 119644-22-3
• Molecular Formula: C₉H₁₀ClFN₂O₄
• Molecular Weight: 264.641
• UNII: 9D65NWY2K0
• DSSTox Substance ID: DTXSID30152541
• Nikkaji Number: J322.524K
• NCI Thesaurus Code: C152150
• Metabolomics Workbench ID: 153790
• ChEMBL ID: CHEMBL2106991
• Mol file: 119644-22-3.mol

Synonyms:3'-fluoro-2',3'-dideoxy-5-chlorouridine;5-chloro-2',3'-dideoxy-3'-fluorouridine;935U83;FddClUrd;raluridine

Chemical Property of Raluridine

Chemical Property:

• Melting Point: 181 °C (decomp)
• PKA: 7.73±0.10(Predicted)
• PSA: 84.32000
• Density: 1.61±0.1 g/cm3(Predicted)
• LogP: -0.19210
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 264.0313127
• Heavy Atom Count: 17
• Complexity: 389

Purity/Quality:

98%,99%, ^*data from raw suppliers

Raluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)Cl)CO)F
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)Cl)CO)F
• Recent ClinicalTrials: The Safety and Effectiveness of 935U83 in HIV-Infected Patients
• Uses: Antiviral. Raluridine is a uridine analogue with activity against HIV-1 and HIV-2 in vitro.

Technology Process of Raluridine

There total 4 articles about Raluridine 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:

5-chloro-1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentodialdofuranosyl)uracil (171074-96-7) → 5-chloro-2',3'-dideoxy-3'-fluorouridine (119644-22-3)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In isopropyl alcohol; at 25 ℃; for 1h; Yield given;

DOI:10.1002/jlcr.2580360802

Reference yield:

(2R,4S,5R)-5-chloro-1-<5-(1,3-diphenyl-2-imidazolidinyl)-4-fluoro-tetrahydro-2-furyl>uracil (171074-97-8) → 5-chloro-2',3'-dideoxy-3'-fluorouridine (119644-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlite IR-118H acidic resin / tetrahydrofuran / 4 h / Ambient temperature

2: NaBH₄, aq. NaOH / propan-2-ol / 1 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; Amberlite IR-118H acidic resin; In tetrahydrofuran; isopropyl alcohol;

DOI:10.1002/jlcr.2580360802

Reference yield:

5'-O-acetyl-2',3'-dideoxy-3'-fluoro-5-chlorouridine (121626-80-0) → 1-(2,3-dideoxy-3-fluoro-β-D-erythro pentofuranos-1-yl)-5-chlorocytosine (127492-32-4) + 5-chloro-2',3'-dideoxy-3'-fluorouridine (119644-22-3)

Guidance literature:

With pyridine; trifluoromethylsulfonic anhydride; ammonia; Yield given. Multistep reaction. Yields of byproduct given; 1.) 1,2-dichloroethane, RT, 3 h, 2.) RT, 15 h;

DOI:10.1021/jm00168a046

upstream raw materials:

5'-O-acetyl-2',3'-dideoxy-3'-fluoro-5-chlorouridine

5-chloro-1-(2,3-dideoxy-3-fluoro-β-D-erythro-pentodialdofuranosyl)uracil

(2R,4S,5R)-5-chloro-1-<5-(1,3-diphenyl-2-imidazolidinyl)-4-fluoro-tetrahydro-2-furyl>uracil

Downstream raw materials:

(2R,4S,5R)-5-chloro-1-<5-(1,3-diphenyl-2-imidazolidinyl)-4-fluoro-tetrahydro-2-furyl>uracil

Refernces

• 1、 Hill,Bankston. "Synthesis of tritium-labelled 5-chloro-2',3'-dideoxy- 3'-fluorouridine (935U83) - A selective anti-HIV agent". . p. 713 - 718. Retrieved 2007/10/02.
• 2、 Aerschot, Arthur Van,Everaert, Dirk,Balzarini, Jan,Augustyns, Koen,Jie, Liu,at al.. "Synthesis and Anti-HIV Evaluation of 2',3'-Dideoxyribo-5-chloropyrimidine Analogues: Reduced Toxicity of 5-Chlorinated 2',3'-Dideoxynucleosides". . p. 1833 - 1839. Retrieved 2007/10/02.