1199809-23-8

Usage

Uses

Used in Pharmaceutical Industry:
((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential applications in treating various diseases.
Used in Stereoselective Synthesis:
In the field of organic chemistry, ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate is used as a key intermediate in the stereoselective synthesis of complex molecules. Its multiple stereocenters and functional groups allow for the creation of enantiomerically pure compounds, which are essential in the development of effective and safe drugs.
Used in Antiviral Drug Development:
((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate has utility in the development of antiviral drugs, particularly for the treatment of hepatitis C virus (HCV) infection. Its related compounds, such as (2R)-2-Deoxy-2-fluoro-2-methyl-α-D-erythro-pentofuranosyl Chloride 3,5-Dibenzoate, are used in the synthesis of prodrugs that target and inhibit the replication of HCV.

Upstream product

• 729596-46-7 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone 
• 30361-18-3 3.5-Di-O-benzoyl-2-C-methyl-α-D-ribofuranose 
• 1199809-22-7 ((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 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 

Relevant academic research and scientific papers

Technology for preparing sofosbuvir intermediate

A technology for preparing a sofosbuvir intermediate represented by formula 1 comprises the following steps: (a) reducing a compound 2 by sodium borohydride to generate a compound 3; (b) reacting thecompound 3 with a methanol-hydrochloric acid solution to generate a compound 4; (c) carrying out a fluorination reaction on the compound 4 and a fluorination reagent in a reaction solvent at -10 to -65 DEG C under the protection of nitrogen, and post-treating a reaction solution after the reaction is fully carried out in order to obtain a compound 5; (d) cooling an n-hexane or petroleum ether or cyclohexane solution of the compound 5 to -5-5 DEG C under the protection of nitrogen, adding thionyl chloride, slowly dropwise adding methanol or ethanol at a controlled temperature of -5-5 DEG C, rising the temperature to 10-40 DEG C after the dropwise addition, continuously performing stirring until the reaction is completed , and removing the solvent to obtain a compound 6; and (e) condensing the compound 6 and a compound 7, and carrying out hydrolysis treatment to obtain the target product which is the compound 1. The preparation technology has the characteristics of high yield, convenience and safety in operation, less discharge of three wastes, low production cost, and suitableness for industrial production.

The synthesis of hydroxyaminopurine nucleosied (by machine translation)

A compound or salt thereof having the following structure useful for the treatment of hepatitis C virus (HCV): wherein R 7 is C 1-6 alkyl or C 3-6 cycloalkyl and R 8 is -O(C 1-6 alkyl) or -O(C 3-6 cycloalkyl).

Stereoselective synthesis of PSI-352938: A β-D -2′-deoxy- 2′-α-fluoro-2′-β-C-methyl-3′,5′-cyclic phosphate nucleotide prodrug for the treatment of HCV

PSI-352938 is a novel 2′-deoxy-2′-α-fluoro-2′- β-C-methyl 3′,5′-cyclic phosphate nucleotide prodrug currently under investigation for the treatment of hepatitis C virus (HCV) infection. PSI-352938 demonstrated superior characteristics in vitro that include broad genotype coverage, superior resistance profile, and high levels of active triphosphate in vivo in the liver compared to our first and second generation nucleoside inhibitors of this class. Consequently, PSI-352938 was selected for further development and an efficient and scalable synthesis was sought to support clinical development. We report an improved, diastereoselective synthesis of a key 1′-β-nucleoside intermediate 13 via SN2 displacement of 1-α-bromo ribofuranose sugar 16 with the potassium salt of 6-chloro-2-amino purine and an efficient method to prepare cis-Rp cyclic phosphate (PSI-352938) in a highly stereoselective manner without any chromatographic purification. The 1-α-bromo sugar 16 was stereospecifically prepared from the corresponding 1-β-lactol in high yield under mild bromination conditions using CBr4/PPh3 (Appel reaction). The desired cis-Rp 3′,5′-cyclic phosphate construction was accomplished using isopropyl phosphorodichloridate readily obtained from POCl3 and isopropyl alcohol. The base combination of Et 3N/NMI was identified as a key factor for producing PSI-352938 as the major (>95%) diastereomer (cis-Rp) in high yield after the final cyclization step. The current route described in this article was successfully used to produce PSI-352938 on multikilogram scale.