Uridine, 2'-deoxy-2'-fluoro-2'-methyl-, (2'R)-

Base Information

• Chemical Name: Uridine, 2'-deoxy-2'-fluoro-2'-methyl-, (2'R)-
• CAS No.: 863329-66-2
• Molecular Formula: C10H13FN2O5
• Molecular Weight: 260.222
• Hs Code.: 2934999090
• European Community (EC) Number: 810-481-6
• UNII: 44V7045CXS
• ChEMBL ID: CHEMBL510394
• DSSTox Substance ID: DTXSID30462011
• Nikkaji Number: J2.995.016D
• Wikidata: Q27258768
• Mol file: 863329-66-2.mol

Synonyms:2'-deoxy-2'-fluoro-2'-C-methyluridine;PSI-6206

Chemical Property of Uridine, 2'-deoxy-2'-fluoro-2'-methyl-, (2'R)-

Chemical Property:

• Appearance/Colour: Off-white solid
• Melting Point: 237-238℃
• PKA: 9.39±0.10(Predicted)
• PSA: 104.55000
• Density: 1.55
• LogP: -1.48460
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 260.08084968
• Heavy Atom Count: 18
• Complexity: 415

Purity/Quality:

99%min. ^*data from raw suppliers

1-[[2'- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=CC(=O)NC2=O)CO)O)F
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O)F
• Description: (2'R)-2'-Deoxy-2'-fluoro-2'-methyluridine / PSI-6206 is the deaminated metabolite of β-D-2'-Deoxy-2'-fluoro-2'-C-methylcytidine, an effective inhibitor of hepatitis C virus (HCV) RNA polymerase.
• Uses: RO 2433 is the deaminated metabolite of β-D-2''-Deoxy-2''-fluoro-2''-C-methylcytidine, an effective inhibitor of hepatitis C virus (HCV) replication in vitro.

Technology Process of Uridine, 2'-deoxy-2'-fluoro-2'-methyl-, (2'R)-

There total 53 articles about Uridine, 2'-deoxy-2'-fluoro-2'-methyl-, (2'R)- 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: 100.0%

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate (863329-65-1) → 2'-deoxy-2'-fluoro-2'-methyluridine (863329-66-2,2041584-99-8)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

DOI:10.1021/jm0502788

Reference yield: 95.0%

C22H41FN2O7Si2 → 2'-deoxy-2'-fluoro-2'-methyluridine (863329-66-2,2041584-99-8)

Guidance literature:

With tetramethylammonium fluoride; acetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Time; Inert atmosphere;

Reference yield: 94.0%

(2'R)-2'-deoxy-2'-fluoro-2'-methyluridine-3',5'-dibenzoate → 2'-deoxy-2'-fluoro-2'-methyluridine (863329-66-2,2041584-99-8)

Guidance literature:

With ammonia; In methanol; at 0 - 15 ℃; for 27h;

upstream raw materials:

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate

(2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate

Downstream raw materials:

sofosbuvir

sofosbuvir

((R)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-pyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-D-alanine isopropyl ester

Refernces

• 1、 -. "Preparation method of anti-hepatitis C medicine sofosbuvir". Paragraph 0052; 0071-0072. . Retrieved 2020/07/02.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF SOFOSBUVIR". Page/Page column 5; 8. . Retrieved 2018/02/20.