Dexelvucitabine

Base Information

• Chemical Name: Dexelvucitabine
• CAS No.: 134379-77-4
• Molecular Formula: C9H10 F N3 O3
• Molecular Weight: 227.195
• UNII: KU8SPJ271W
• DSSTox Substance ID: DTXSID20158678
• Nikkaji Number: J1.064.022I
• Wikipedia: Dexelvucitabine
• Wikidata: Q5268320
• NCI Thesaurus Code: C76928
• Metabolomics Workbench ID: 153454
• ChEMBL ID: CHEMBL109831
• Mol file: 134379-77-4.mol

Synonyms:2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine;2',3'-dideoxy-2',3'-didehydro-beta-D-5-fluorocytidine;2',3'-dideoxy-2',3'-didehydro-beta-L-5-fluorocytidine;2(1H)-Pyrimidinone, 4-amino-1-((2S,5R)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl)-5-fluoro-;4-amino-5-fluoro-1-((2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl)pyrimidin-2(1H)-one;ACH-126-443;beta-D-D4FC;beta-L-Fd4C;D-D4FC;dexelvucitabine;DPC 817;DPC-817;DPC817;elvucitabine;INCB-8721;L-D4FC;Reverset

Chemical Property of Dexelvucitabine

Chemical Property:

• Vapor Pressure: 7.15E-08mmHg at 25°C
• Boiling Point: 394.9°Cat760mmHg
• PKA: 14.28±0.10(Predicted)
• Flash Point: 192.6°C
• PSA: 90.37000
• Density: 1.66g/cm³
• LogP: -0.00830
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 227.07061935
• Heavy Atom Count: 16
• Complexity: 405

Purity/Quality:

97% ^*data from raw suppliers

Dexelvucitabine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(OC1CO)N2C=C(C(=NC2=O)N)F
• Isomeric SMILES: C1=C[C@@H](O[C@@H]1CO)N2C=C(C(=NC2=O)N)F
• Recent ClinicalTrials: Randomized, Double-Blind Study Comparing Dexelvucitabine (DFC) to Lamivudine (3TC) in Subjects With Resistance to NRTIs, PIs, and NNRTIs
• Recent EU Clinical Trials: A Randomized, Double-Blind, Phase II Study Comparing the Anti-Retroviral Safety and Efficacy of Dexelvucitabine (DFC) 200 mg Once Daily to Lamivudine (3TC) 300 mg Once Daily in Addition to Optimized Background Therapy in HIV-1 Infected Subjects Who Have Failed and/or Harbor HIV with Resistance Mutations to NRTIs, PIs, and NNRTIs
• Uses: Treatment of HIV-1 and HIV-2 infection. Dexelvucitabine is a nucleoside reverse transcriptase inhibitor (NRTI) which had the potential to inhibit HIV-1 replication. The drug was discontinued due to evidence that it causes damage to the pancreas.

Technology Process of Dexelvucitabine

There total 17 articles about Dexelvucitabine 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: 93.0%

β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (221156-15-6) → β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (134379-77-4,181785-84-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1021/jm980510s

Reference yield: 83.0%

5′-O-(α-acetoxyisobutyryl)-2′,3-didehydro-2′,3′-dideoxy-5-fluorocytidine → β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (134379-77-4,181785-84-2)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 16h; Reagent/catalyst;

Reference yield: 82.0%

4-methoxybenzoic acid 5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydrofuran-2-ylmethyl ester (869383-89-1) → β-D-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine (134379-77-4,181785-84-2)

Guidance literature:

With sodium methylate; In methanol; for 19h;

DOI:10.1016/j.tetlet.2005.09.139

upstream raw materials:

Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester

β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine

4-methoxybenzoic acid 5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydrofuran-2-ylmethyl ester

1,4-anhydro-3',5'-di-p-methoxybenzoyloxy-2-deoxy-D-threo-pent-1-enitol

Downstream raw materials:

(2-furyl)methyl alcohol

Flucytosine

Refernces

• 1、 -. "Method for the synthesis of 2',3'-dideoxy-2',3'-didehydronucleosides". . . Retrieved 2008/06/13.
• 2、 Chen, Shu-Hui,Lin, Stanley,King, Ivan,Spinka, Tracy,Dutschman, Ginger E.,Gullen, Elizabeth A.,Cheng, Yung-Chi,Doyle, Terrence W.. "Synthesis and comparative evaluation of two antiviral agents: β-L- Fd4C and β-D-Fd4C". . p. 3245 - 3250. Retrieved 2007/10/03.