Pharmaceutical intermediates

863329-66-2

  • Product Name:2'-deoxy-2'-fluoro-2'-C-methyluridine
  • Molecular Formula:C10H13FN2O5
  • Specifications:99%
  • Molecular Weight:260.222
Inquiry

Product Details;

CasNo: 863329-66-2

Molecular Formula: C10H13FN2O5

Appearance: Off-white solid

Hot Sale Top Purity 2'-deoxy-2'-fluoro-2'-C-methyluridine 863329-66-2 Powder

  • Molecular Formula:C10H13FN2O5
  • Molecular Weight:260.222
  • Appearance/Colour:Off-white solid 
  • Melting Point:237-238℃ 
  • PKA:9.39±0.10(Predicted) 
  • PSA:104.55000 
  • Density:1.55 
  • LogP:-1.48460 

2'-deoxy-2'-fluoro-2'-C-methyluridine(Cas 863329-66-2) Usage

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

2'-deoxy-2'-fluoro-2'-C-methyluridine 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.

Biological Activity

In contrast, the average concentration of 2'-deoxy-2'-fluoro-2'-C-methyluridine in CSF samples after i.v. administration was 1.5 ± 0.8 μM. However, the concentration of 2'-deoxy-2'-fluoro-2'-C-methyluridine in CSF samples was below the limit of detection (≤0.38 μM) following oral administration.

Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O)F  
InChIKey: ARKKGZQTGXJVKW-VPCXQMTMSA-N  
InChI: InChI=1S/C10H13FN2O5/c1-10(11)7(16)5(4-14)18-8(10)13-3-2-6(15)12-9(13)17/h2-3,5,7-8,14,16H,4H2,1H3,(H,12,15,17)/t5-,7-,8-,10-/m1/s1  

863329-66-2 Relevant articles

Pharmacokinetics of the Antiviral Agent β-d-2′-Deoxy-2′-Fluoro-2′-C-Methylcytidine in Rhesus Monkeys

Ghazia Asif, Selwyn J. Hurwitz, Junxing Shi, Brenda I. Hernandez-Santiago, Raymond F. Schinazi

Antimicrobial Agents and Chemotherapy Vol. 51, No. 8

The total bioavailability, taking into account the parent drug and its deaminated metabolite 2′-deoxy-2′-fluoro-2′-C-methyluridine (PSI-6206),

Preparation method of anti-hepatitis C medicine sofosbuvir

-

Paragraph 0052; 0071-0072, (2020/07/02)

The invention discloses a preparation me...

Preparation method of sofosbuvir key intermediate

-

Paragraph 0013, (2020/05/01)

The invention belongs to the technical f...

A 2′-deoxy-2′-fluoro-2′-C-methyl uridine cyclopentyl carbocyclic analog and its phosphoramidate prodrug as inhibitors of HCV NS5B polymerase

Jian Liu,Jinfa Du,Peiyuan Wang,Dhanapalan Nagarathnam,Christine L. Espiritu,Haiying Bao,Eisuke Murakami,Phillip A. Furman &Michael J. Sofia

Nucleosides, Nucleotides & Nucleic Acids Volume 31, 2012 - Issue 4

As part of our SAR study of the 2  ′-deoxy-2  ′-fluoro-2  ′- C-methyl class of nucleosides, we prepared the cyclopentyl carbocyclic uridine analog 11 and its phosphoramidate prodrug 15. Both 11 and 15 were shown not to inhibit HCV replication.

863329-66-2 Process route

(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate
863329-65-1

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

2'-deoxy-2'-fluoro-2'-methyluridine
863329-66-2,2041584-99-8

2'-deoxy-2'-fluoro-2'-methyluridine

Conditions
Conditions Yield
With ammonia; In methanol; at 20 ℃;
100%
With ammonia; In methanol; at 20 ℃; for 17h;
93%
With methanol; triethylamine; for 53h; Reflux;
93.8%
(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate; With N-butylamine; at 45 - 50 ℃;
With methanol; In tert-butyl methyl ether; at 60 - 70 ℃;
90.7%
With sodium methylate; In methanol; Reagent/catalyst; Reflux;
82.6%
With ammonia; In methanol; at 0 - 15 ℃; for 27h;
78%
With ammonia; In methanol; at 0 - 15 ℃; for 27h;
78%
With ammonia; In methanol; at 0 - 15 ℃; for 27h;
78%
With methanol; ammonia; at 20 ℃; for 30h;
62%
With ammonia; In methanol; at 0 - 20 ℃; for 18.5h;
60%
With methanol; ammonia; at 0 - 20 ℃;
60%
(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate; With sodium methylate; In methanol; at -10 - 20 ℃; for 2h; Inert atmosphere; Large scale;
With sulfuric acid; In methanol; at -10 ℃; Large scale;
59.15%
(2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate; With sodium methylate; In methanol; at -10 - 20 ℃; for 2h; Inert atmosphere; Large scale;
With sulfuric acid; In methanol; at -10 ℃; Large scale;
59.15%
With sodium methylate; In methanol; Temperature; Reflux;
 
With methanol; ammonia; at 0 - 15 ℃; for 27h;
35 g
With monomethanolamine; at 25 - 30 ℃; for 24h;
3 g
With sodium methylate; In methanol; Reflux;
 
With ammonia; at 0 - 15 ℃; for 20h;
55 g
With ammonia; In methanol;
 
(2'R)-2'-deoxy-2'-fluoro-2'-methyluridine-3',5'-dibenzoate

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

2'-deoxy-2'-fluoro-2'-methyluridine
863329-66-2,2041584-99-8

2'-deoxy-2'-fluoro-2'-methyluridine

Conditions
Conditions Yield
With ammonia; In methanol; at 0 - 15 ℃; for 27h;
94%
With methanol; triethylamine; for 53h; Reflux;
92.6%

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863329-66-2 Downstream products

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