2041584-99-8

Basic information

• Product Name: 1-((2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• Synonyms: SofosBuvir Impurity 10
• CAS NO: 2041584-99-8
• Molecular Formula: C10H13FN2O5
• Molecular Weight: 260.2190232
• Mol File: 2041584-99-8.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• Density: 1.55±0.1 g/cm3(Predicted)
• PKA: 9.39±0.10(Predicted)
• CAS DataBase Reference: 1-((2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione(2041584-99-8)
• EPA Substance Registry System: 1-((2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione(2041584-99-8)

Safety Data

• Hazardous Substances Data: 2041584-99-8(Hazardous Substances Data)

Usage

General Description

1-((2S,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione is a chemical compound with a pyrimidine ring structure and a fluorine atom attached to the furan ring. It also contains hydroxyl and methyl groups, as well as a keto group. This chemical has potential biological activity due to its structural features, such as its ability to interact with enzymes or receptors in living systems. It may have implications in drug development or medicinal chemistry, as well as in studies of biochemical and physiological processes. In addition, it may be used as a reference standard in chemical analysis or as a starting material in organic synthesis.

Upstream product

• 3736-77-4 2,2'-Anhydrouridine 
• 58-96-8 uridine 
• 944476-40-8 (2R,3R,3aS,9aR)-3-hydroxy-2-(hydroxymethyl)-3a-methyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 31448-54-1 2'-C-methyluridine 
• 23643-36-9 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine 
• 7392-74-7 (3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 
• 944476-44-2 C₂₄H₂₂N₂O₈ 
• 54618-11-0 3’,5’-dibenzoyluridine 
• 31616-01-0 3’,5’-O-benzoyl-2,2’-anhydrouridine 
• 944476-43-1 C₂₄H₂₀N₂O₇ 
• 114262-49-6 1-(2'-C-methyl-β-D-arabinofuranosyl)uracil 
• 874638-93-4 (2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate 
• 874638-80-9 ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 1496552-16-9 ((S)-(((2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-pyrimidin-1(2H)-yl)-4-fluoro-3-hydroxy-4-methyl-tetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-D-alanine isopropyl ester 

Relevant articles and documents

Design, synthesis, and antiviral activity of 2′-deoxy-2′- fluoro-2′-C-methylcytidine, a potent inhibitor of hepatitis C virus replication

The pyrimidine nucleoside beta-D-2′-deoxy-2′-fluoro-2′-C- methylcytidine (1) was designed as a hepatitis C virus RNA-dependent RNA polymerase (HCV RdRp) inhibitor. The title compound was obtained by a DAST fluorination of N4-benzoyl-1-(2-methyl-3,5-di-O-benzoyl-β-D- arabinofuranosyl]cytosine (6) to provide N4-benzoyl-1-[2-fluoro-2- methyl-3,5-di-O-benzoyl-β-D-ribofuranosyl]cytosine (7a). The protected 2′-C-methylcytidine (7c) was obtained as a byproduct from the DAST fluorination and allowed for the preparation of two biologically active compounds from a common precursor. Compound 1 and 2′-C-methylcytidine were assayed in a subgenomic HCV replicon assay system and found to be potent and selective inhibitors of HCV replication. Compound 1 shows increased inhibitory activity in the HCV replicon assay compared to 2′-C-methylcytidine and low cellular toxicity.

Preparation method of anti-hepatitis C medicine sofosbuvir

The invention discloses a preparation method of an anti-hepatitis C medicine sofosbuvir. The method comprises the following steps: taking r-ethyl glycerate acetonide as an initial raw material, enabling the r-ethyl glycerate acetonide to react with ethyl alpha-fluoropropionate under the action of potassium tert-butoxide, performing carbonyl reduction, hydroxyl acylation, hydrolytic cyclization under an acidic condition, hydroxyl acylation, red aluminum reduction and chiral column separation so as to obtain a sofosbuvir key intermediate ((2R,3R,4R,5R)-3-(benzoyloxy)-5-hydroxy-4-fluoro-4-methyltetrahydrofuran-2-yl) methyl benzoate, performing 2-hydroxyl acetylation, enabling acetylized material to react with 2-trimethylsiloxy-4-benzamidopyrimidine, removing benzamido under an acidic condition, performing dehydroxylation protection, and finally enabling obtained material to react with N-[(S)-(2,3,4,5,6-Pentafluorophenoxy)phenoxyphosphinyl]-L-alanine 1-methylethyl ester to obtain the sofosbuvir. The method has the advantages of short synthesis route, high yield, avoidance of a fluorination reaction step in the synthesis process, and mild synthesis reaction conditions.

Preparation method of sofosbuvir key intermediate

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a sofosbuvir key intermediate. The preparation method of the sofosbuvir intermediate hasthe advantages of short reaction steps, mild reaction conditions and higher yield than that of an existing preparation method, is economical and effective, and is suitable for large-scale industrial production.