Elvucitabine

Base Information

• Chemical Name: Elvucitabine
• CAS No.: 181785-84-2
• Molecular Formula: C₉H₁₀FN₃O₃
• Molecular Weight: 227.195
• UNII: M09BUF90C0
• DSSTox Substance ID: DTXSID20171185
• Nikkaji Number: J746.100C
• Wikipedia: Elvucitabine
• Wikidata: Q1334337
• NCI Thesaurus Code: C73201
• Metabolomics Workbench ID: 149695
• ChEMBL ID: CHEMBL38700
• Mol file: 181785-84-2.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 Elvucitabine

Chemical Property:

• Vapor Pressure: 7.15E-08mmHg at 25°C
• Boiling Point: 394.9°C at 760 mmHg
• 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

Elvucitabine ^*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: Safety and Antiviral Activity Study of ACH-126,443 (Beta-L-Fd4C) in Treatment-naive Adults With Chronic Hepatitis B Virus Infection
• Recent EU Clinical Trials: Immune reconstitution in severely immunosuppressed antiretroviral-naive HIV-1?infected patients (<100 CD4+ T cells/?L) taking antiretroviral regimens based on dolutegravir or ritonavir-boosted darunavir (the AdvanZ-4 Trial).
• Uses: A novel antiviral agent A novel antiviral agent.

Technology Process of Elvucitabine

There total 38 articles about Elvucitabine 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: 94.0%

4-Amino-1-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-5-fluoro-1H-pyrimidin-2-one (189818-66-4) → elvucitabine (181785-84-2)

Guidance literature:

With triethylamine trihydrofluoride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1021/jo970177k

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: 88.0%

2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine (1382683-49-9) → α-elvucitabine (181785-84-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1080/00397911.2011.571805

upstream raw materials:

4-Amino-1-(1S,3S,5S)-2,6-dioxa-bicyclo[3.2.0]hept-3-yl-5-fluoro-1H-pyrimidin-2-one

4-Amino-1-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-5-fluoro-1H-pyrimidin-2-one

(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose