874638-93-4

Basic information

• Product Name: (2R,3R,4R,5R)-5-Acetoxy-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
• Synonyms: (2R,3R,4R,5R)-5-Acetoxy-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
• CAS NO: 874638-93-4
• Molecular Formula: C₂₂H₂₁FO₇
• Molecular Weight: 416.3963432
• Mol File: 874638-93-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R,3R,4R,5R)-5-Acetoxy-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4R,5R)-5-Acetoxy-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate(874638-93-4)
• EPA Substance Registry System: (2R,3R,4R,5R)-5-Acetoxy-2-(benzoyloxymethyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate(874638-93-4)

Safety Data

• Hazardous Substances Data: 874638-93-4(Hazardous Substances Data)

Upstream product

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

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 
• 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 
• 1393443-71-4 4-chloro-7-((2R)-3,5-di-O-benzoyl-2-deoxy-2-fluoro-2-methyl-α-D-ribofuranosyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 1393444-07-9 C₂₆H₃₁FN₇O₇P 
• 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 
• 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) 
• 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 
• 863329-65-1 3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-2'-C-methyluridine 

Relevant articles and documents

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.

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.

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.