874638-93-4

Upstream product

• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 874638-80-9 ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 817204-32-3 (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate 
• 863329-65-1 (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate 
• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 
• 1621160-34-6 ((2R,3R,4R,5R)‐3‐(benzoyloxy)‐5‐(2,4‐dioxo‐3,4‐dihydro‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐4‐fluoro‐4‐methyltetrahydrofuran‐2‐yl)methyl benzoate 
• 1621160-32-4 (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate 
• 1233335-84-6 ((2R,3R,4R,5S)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 1199809-24-9 (((2R,3R,4R,5R)-3-(benzoyloxy)-5-bromo-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate) 
• 863329-65-1 3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methyluridine 
• 1393444-07-9 C₂₆H₃₁FN₇O₇P 
• 1256339-79-3 ((2R,3R,4R,5R)-3-(benzoyloxy)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate 

Relevant academic research and scientific papers

Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs

Novel 7-trifluoromethyl-7-deazapurine ribonucleoside analogs (13a-c) and their Protides (15a-c) were successfully synthesized from ribolactol or 1-α-bromo-ribose derivatives using Silyl-Hilbert-Johnson or nucleobase-anion substitution reactions followed by key aromatic trifluoromethyl substitution. Newly prepared compounds were evaluated against a panel of RNA viruses, including HCV, Ebola or Zika viruses.

Deuterated nucleoside derivative

The present invention relates to deuterated nucleoside derivative, particularly to a compound having a structure represented by a formula I or a pharmaceutically acceptable salt thereof. According to the present invention, the compound represented by the formula I has excellent pharmacokinetic properties and is expected to reduce the clinical dose so as to reduce the treatment and benefit more patients. The formula I is defined in the specification.

Aspartic acid based nucleoside phosphoramidate prodrugs as potent inhibitors of hepatitis C virus replication

In view of a persistent threat to mankind, the development of nucleotide-based prodrugs against hepatitis C virus (HCV) is considered as a constant effort in many medicinal chemistry groups. In an attempt to identify novel nucleoside phosphoramidate analogues for improving the anti-HCV activity, we have explored, for the first time, aspartic acid (Asp) and iminodiacetic acid (IDA) esters as amidate counterparts by considering three 2′-C-methyl containing nucleosides, 2′-C-Me-cytidine, 2′-C-Me-uridine and 2′-C-Me-2′-fluoro-uridine. Synthesis of these analogues required protection for the vicinal diol functionality of the sugar moiety and the amino group of the cytidine nucleoside to regioselectively perform phosphorylation reaction at the 5′-hydroxyl group. Anti-HCV data demonstrate that the Asp-based phosphoramidates are ～550 fold more potent than the parent nucleosides. The inhibitory activity of the Asp-ProTides was higher than the Ala-ProTides, suggesting that Asp would be a potential amino acid candidate to be considered for developing novel antiviral prodrugs.

NOVEL ANTIVIRAL AND ANTITUMORAL COMPOUNDS

The present invention relates to novel phosphate-modified nucleosides, such as phosphoramidate nucleosides. The invention also relates to the use of these novel phosphate-modified nucleosides to treat or prevent viral infections and proliferative diseases

An efficient and diastereoselective synthesis of PSI-6130: A clinically efficacious inhibitor of HCV NS5B polymerase

(Chemical Equation Presented) R7128 is the prodrug of 2′-deoxy- 2′-fluoro-2′-C-methylcytidine (PSI-6130), a potent and selective inhibitor of HCV NS5B polymerase. Currently, R7128 is in clinical trials for the treatment of HCV infection. To support clinical development efforts, we needed an efficient and scalable synthesis of PSI-6130. We describe an improved, diastereoselective synthetic route starting with protected D-glyceraldehyde. No chiral reagents or catalysts were used to produce the three new contiguous stereocenters. Introduction of fluorine at the C-2 tertiary carbon was accomplished in a highly regio- and stereoselective manner through nucleophilic substitution on a cyclic sulfate. Scale-limiting chromatographic purifications were eliminated through the use of crystalline intermediates.

PREPARATION OF 2'-FLUORO-2'- ALKYL- SUBSTITUTED OR OTHER OPTIONALLY SUBSTITUTED RIBOFURANOSYL PYRIMIDINES AND PURINES AND THEIR DERIVATIVES

The present invention provides (i) processes for preparing a 2'-deoxy-2'-fluoro-2'-methyl-D-ribonolactone derivatives, (ii) conversion of intermediate lactones to nucleosides with potent anti-HCV activity, and their analogues, and (iii) methods to prepare the anti-HCV nucleosides containing the 2'-deoxy-2'-fluoro-2'-C--methyl-β-D-ribofuranosyl nucleosides from a preformed, preferably naturally--occurring, nucleoside.