863329-65-1

Usage

Uses

Used in Antiviral Applications:
(2'R)-2'-Deoxy-2'-fluoro-2'-Methyl-uridine 3',5'-dibenzoate is used as an antiviral agent for its ability to inhibit the replication of certain viruses, such as the hepatitis C virus (HCV). It functions as a deaminated metabolite of β-D-2''-Deoxy-2''-fluoro-2''-C-methylcytidine, which has demonstrated effectiveness in inhibiting HCV replication in vitro.
Used in Pharmaceutical Industry:
(2'R)-2'-Deoxy-2'-fluoro-2'-Methyl-uridine 3',5'-dibenzoate is used as a key intermediate in the synthesis of various nucleoside analogs and antiviral drugs. Its unique chemical structure allows for the development of new therapeutic agents with improved efficacy and reduced side effects.
Used in Research and Development:
(2'R)-2'-Deoxy-2'-fluoro-2'-Methyl-uridine 3',5'-dibenzoate is used as a research compound for studying the mechanisms of viral replication and the development of resistance to antiviral drugs. It can also be employed as a tool to investigate the structure-activity relationships of nucleoside analogs and their potential applications in medicine.

Upstream product

• 1500076-79-8 (2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate 
• 31616-01-0 3’,5’-O-benzoyl-2,2’-anhydrouridine 
• 54618-11-0 3’,5’-dibenzoyluridine 
• 944476-44-2 C₂₄H₂₂N₂O₈ 
• 944476-43-1 C₂₄H₂₀N₂O₇ 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 7392-74-7 (3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate 
• 23643-36-9 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine 
• 58-96-8 uridine 
• 3736-77-4 2,2'-Anhydrouridine 
• 879551-04-9 (3R,4R,5R)-3?fluoro?4?hydroxy?5?(hydroxymethyl)?3?methyltetrahydrofuran?2?one 
• 914912-73-5 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose 
• 66-22-8 uracil 
• 874638-93-4 (2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate 

Downstream Products

• 1064684-23-6 (S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}-3-methylbutyric acid methyl ester 
• 1064684-25-8 (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 
• 1064684-24-7 (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 
• 2041584-99-8 1-[(2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-hydroxymethyl-3-methyltetrahydrofuran-2-yl]pyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Structure-activity relationship of uridine-based nucleoside phosphoramidate prodrugs for inhibition of dengue virus RNA-dependent RNA polymerase

To identify a potent and selective nucleoside inhibitor of dengue virus RNA-dependent RNA polymerase, a series of 2′- and/or 4′-ribose sugar modified uridine nucleoside phosphoramidate prodrugs and their corresponding triphosphates were synthesized and evaluated. Replacement of 2′-OH with 2′-F led to be a poor substrate for both dengue virus and human mitochondrial RNA polymerases. Instead of 2′-fluorination, the introduction of fluorine at the ribose 4′-position was found not to affect the inhibition of the dengue virus polymerase with a reduction in uptake by mitochondrial RNA polymerase. 2′-C-ethynyl-4′-F-uridine phosphoramidate prodrug displayed potent anti-dengue virus activity in the primary human peripheral blood mononuclear cell-based assay with no significant cytotoxicity in human hepatocellular liver carcinoma cell lines and no mitochondrial toxicity in the cell-based assay using human prostate cancer cell lines.

AN IMPROVED PROCESS FOR THE PREPARATION OF SOFOSBUVIR

The present invention relates to an improved, commercially viable and industrially advantageous process for the preparation of Sofosbuvir. The present invention involves use of reagents that are less expensive, easier to handle and eco-friendly process.

Nucleoside phosphoramidate compound optical isomer and its application

The invention belongs to the field of medicinal chemistry, and in particular relates to a nucleoside phosphoramidate compound optical isomer or its hydrate, solvate, crystal or a pharmaceutically acceptable salt, process for their preparation and pharmaceutical compositions containing these compounds and these compounds or compositions used as virus infectious disease treating drug use, in particular as viral hepatitis treatment drug use. The experimental result shows, the compounds of this invention to hepatitis c virus 1 b subtype and 1 a subtype exhibit good inhibitory activity, while at the same time to the host cell has very low toxicity, high effectiveness, the safety is good, suitable for the treatment and/or prevention of diseases associated with HCV infection.

Biphenyl nucleoside phosphoramidate application of compound

The invention belongs to the field of medicinal chemistry, provided the present invention of the formula 1 compound or its pharmaceutically acceptable salt, solvate, hydrate, stereoisomer or crystallization in preparation for the treatment of flavivirus, especially hepatitis c virus infection after the drug resistance of the patient, and/or prevention of drug-resistant patient disease onset or recurrence of the application of the medicament. The invention of the formula 1 compound has good medicine chest activity of HCV.

Preparation method of (2'R)-2'-deoxy-2'-fluoro-2'-methyluridine

The invention relates to the technical field of medicinal chemistry, in particular to a preparation method of (2'R)-2'-deoxy-2'-fluoro-2'-methyluridine. According to the method, (2R)-2-deoxy-2-fluoro-2-methyl-D-erythropentonic acid GAMMA-lactone is taken as a raw material and is subjected to reduction and protection, a fluoro ribose fragment with three identical protection groups is obtained and directly reacts with uracil, deprotection is performed, and a target compound is obtained. Compared with an existing technical route adopting an eight-step reaction, the route of the preparation method is shortened to adopt four steps, and the problems that the existing technical route adopts complicated steps, the atom economy is low, the cost is high and the like are effectively solved; besides, an obtained intermediate can be recrystallized and refined, the whole route is simple, and the method is convenient to operate, high in yield and suitable for large-scale industrial production.

A (2 'R) -2' - deoxy -2 '- fluoro -2' - methyl urea glucoside preparation method (by machine translation)

The invention discloses a (2 'R) -2' - deoxy -2 '- fluoro -2' - methyl urea glucoside (type I) synthetic method. Cheap and easily available starting material, through the hydroxyl protection, cyclization, the links such as fluoride, obtains the type I compound. (by machine translation)

Intermediate compound for synthesis of sofosbuvir and synthetic method thereof

The invention discloses an intermediate compound for synthesis of sofosbuvir and a synthetic method thereof; the intermediate compound comprises 4 intermediate products and 1 target compound, wherein the 4 intermediate products include methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl) benzoate, methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-chloro-4-methyltetrahydrofuran-2-yl) benzoate, (2'R)-N-benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine 3',5'-dibenzoate, and ((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methyltetrahydrofuran-2-yl) methyl benzoic acid, and the target compound is (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine. Compared with existing synthetic methods, the synthetic method has high content of target compound and has little impurities generated in the synthetic process; the results of the synthetic method are stable, the synthetic method is simple to perform and is applicable to large-scale industrial production and technical popularization.

Synthesis method of sofosbuvir

The invention provides a synthesis method of sofosbuvir. The synthesis method of the sofosbuvir comprises the following steps: performing mitsunobu reaction on ((2R,3R,4R)-3-benzoyloxy)-4-fluorine-5-hydroxyl-4-methyltetrahydrofuran-2-yl)methyl benzoate to produce sulfonate to obtain a compound 1; abutting the compound 1 and N-benzoylcytosine to produce a compound 2. The method adopts mitsunobu reaction to avoid production of an isomer, and the isomer is reduced to 5 percent or below; according to the method, sulfonate and N-benzoylcytosine are abutted, so the use ofa stannic chloride raw material is avoided; furthermore, the yield is high and few solid waste is generated during aftertreatment, so that the method is suitable for large-scale industrialized production.

A nucleoside phosphoramide prodrug and its preparation method and its application

The invention relates to a nucleoside phosphamide prodrug as well as a preparation method and application of the nucleoside phosphamide prodrug. The nucleoside phosphamide prodrug is selected from any one of a compound I and a compound II, wherein in the formulas of the compound I and the compound II, X is selected from any one of F, Cl, Br and I. Compared with GS7977andGS7851, The compound I or II disclosed by the invention has more excellent resistance to hepatitis C virus, wherein the formulas I and II are respectively as shown in specifications.

A ribofuranose method for the preparation of phosphoric acid ester derivative

Disclosed in the present invention is a method for preparing ribofuranose phosphate derivatives, and the preparation steps thereof comprises: coupling starting materials of isopropyl L-alanine hydrochloride, phenol dichlorophosphate and substituted phenol under the action of alkali; reducing carbonyl into alcoholic hydroxyl by means of treating (2R)-2-deoxy-2-fluoro-2-methyl-D-erythro pentonic acid GAMMA-lactone 3,5-dibenzoate with a strong reducing agent in the solvent of dichloromethane or ethers; reacting the intermediate of formula 2-1 with p-toluene sulfonyl chloride under the action of alkali to obtain p-toluene sulfonate; coupling the intermediate of formula 2-2 with a benzoyl cytosine derivative under the action of a condensation agent; converting cytosine of the intermediate of formula 2-3 into uracil under the action of an organic acid; removing benzoyl acting as protecting group from the intermediate of formula 2-4 under the action of an alkaline reagent; and coupling the intermediate of formula 2-5 with formula 1 under the action of a Grignard reagent to obtain Sofosbuvir.