2'-deoxy-2'-fluoro-2'-C-methylcytidine

Base Information

• Chemical Name: 2'-deoxy-2'-fluoro-2'-C-methylcytidine
• CAS No.: 817204-33-4
• Molecular Formula: C10H14FN3O4
• Molecular Weight: 259.237
• UNII: 05J68784G1
• DSSTox Substance ID: DTXSID10231287
• Nikkaji Number: J2.525.416C
• Wikipedia: PSI-6130
• Wikidata: Q7120654
• ChEMBL ID: CHEMBL223482
• Mol file: 817204-33-4.mol

Synonyms:2'-deoxy-2'-fluoro-2'-C-methylcytidine;2'-F-2'-C-MeC;4-amino-(3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidin-2(1H)-one;PSI 6130;PSI-6130;PSI6130

Chemical Property of 2'-deoxy-2'-fluoro-2'-C-methylcytidine

Chemical Property:

• Appearance/Colour: Pale brown solid
• Melting Point: 216-218℃
• Boiling Point: 482.4±55.0 °C(Predicted)
• PKA: 12.86±0.70(Predicted)
• PSA: 110.60000
• Density: 1.67
• LogP: -0.61450
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 259.09683410
• Heavy Atom Count: 18
• Complexity: 427

Purity/Quality:

98% ^*data from raw suppliers

PSI6130 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(C(OC1N2C=CC(=NC2=O)N)CO)O)F
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)CO)O)F
• Description: PSI-6130 is a nucleoside inhibitor of the NS5B RNA polymerase of hepatitis C virus (HCV; Ki = 4.3 μM). It inhibits HCV genotype 1b (GT-1b) Con1 and GT-1a H77 viral replication in Huh7 replicon cells using a luciferase-based assay (EC50s = 0.51 and 0.30 μM, respectively). PSI-6130 also inhibits replication of HCV GT-1b and GT-1a replicons from clinical isolates, with EC50 values ranging from 0.60 to 1.41 μM, and 0.20 to 0.43 μM, respectively, in the same assay. It has little or no activity against West Nile Virus (WNV), Dengue type 2 virus (DV), human immunodeficiency virus (HIV), or hepatitis B virus (HBV; EC90s = 46.3, >100, >100, and >10 μM, respectively).
• Uses: PSI-6130 is an experimental treatment for hepatitis C. PSI-6130 is a member of a class of antiviral drugs known as nucleoside polymerase inhibitors. PSI-6130 inhibits the hepatitis C virus RNA dependant RNA polymerase called NS5B.

Technology Process of 2'-deoxy-2'-fluoro-2'-C-methylcytidine

There total 12 articles about 2'-deoxy-2'-fluoro-2'-C-methylcytidine 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: 91.0%

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate (817204-32-3) → (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine (817204-33-4)

Guidance literature:

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate; With sodium methylate; In methanol; at 60 ℃; for 4h;

With isobutyric Acid; In methanol;

Reference yield: 76.0%

C33H30FN3O5 → (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine (817204-33-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

Reference yield: 76.0%

C30H24FN3O8 → (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine (817204-33-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

upstream raw materials:

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

(3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyldihydrofuran-2(3H)-one

N-(1-((2R,3R,4R,5R)-5-(benzyloxymethyl)-4-(tert-butyldimethylsilyloxy)-3-fluoro-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

C₂₃H₃₂FN₃O₅Si

Downstream raw materials:

mericitabine

(S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

(S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2-oxo-3-aminopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester

(S)-2-{(4-bromophenoxy)[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}propionic acid methyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF 2-DEOXY-2-FLUORO-2-METHYL-D-RIBOFURANOSYL NUCLEOSIDE COMPOUNDS". Page/Page column 12. . Retrieved 2014/01/07.
• 2、 -. "METHODS FOR TREATING HCV". Paragraph 0360. . Retrieved 2013/10/22.