233266-76-7

Upstream product

• 153186-10-8 ((3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol 
• 100-39-0 benzyl bromide 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 79-37-8 oxalyl dichloride 
• 2595-05-3 Diacetone D-glucose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 22393-62-0 BnBr 

Downstream Products

• 233266-77-8 3,5-di-O-benzyl-4-C-(2,2-dibromoethenyl)-1,2-O-isopropylidene-α-D-ribo-pentofuranose 
• 1095153-37-9 3,5-di-O-benzyl-4-C-(1-hydroxy-allyl)-1,2-O-isopropylidene-α-D-ribofuranose 
• 1095154-25-8 3,5-di-O-benzyl-4-C-(1-hydroxy-but-3-enyl)-1,2-O-isopropylidene-α-D-ribofuranose 
• 1610605-74-7 (2R,3R,4S,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzyloxy)-5-((benzyloxy)methyl)-5-(2-(tosyloxy)ethyl)tetrahydrofuran-3-yl acetate 
• 1610605-75-8 2-amino-9-((1R,5R,7R,8S)-8-(benzyloxy)-5-((benzyloxy)methyl)-2,6-dioxabicyclo[3.2.1]octan-7-yl)-1H-purin-6(9H)-one 
• 287737-63-7 (3aR,5R,6S,6aR)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole 
• 865363-93-5 (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol monohydrate 
• 1146197-36-5 (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-2,3-diyl diacetate 
• 233266-85-8 (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate 
• 233266-94-9 1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 233266-86-9 (2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-5-((triethylsilyl)ethynyl)tetrahydrofuran-3-yl acetate 
• 233266-95-0 1-((2R,3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-3-hydroxy-5-((triethylsilyl)ethynyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 
• 233266-82-5 1,2-di-O-acetyl-3,5-di-O-benzyl-4-C-triethylsilylethynyl-D-ribo-pentofuranose 

Relevant academic research and scientific papers

METHOD FOR PRODUCING NUCLEOSIDE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a practical method for producing a nucleoside derivative that is applied to RNA pharmaceuticals or the like. SOLUTION: The present invention provides a method for producing a nucleotide derivative represented by a compound

Synthesis of EFdA via a diastereoselective aldol reaction of a protected 3-keto furanose

An efficient enantioselective total synthesis of EFdA, a remarkably potent anti-HIV nucleoside analogue with various favorable pharmacological profiles, has been achieved in 37% overall yield from diacetone-d-glucose by a 14-step sequence that features a

PYRROLO[1,2-f][1,2,4]TRIAZINES USEFUL FOR TREATING RESPIRATORY SYNCITIAL VIRUS INFECTIONS

Provided herein are formulations, methods and substituted tetrahydrofuranyl-pyrrolo[1,2-f][1,2,4]triazine-4-amine compounds of Formula (I) for treating Pneumovirinae virus infections, including respiratory syncytial virus infections, as well as methods and intermediates for synthesis of tetrahydrofuranyl-pyrrolo[1,2-f][1,2,4]triazine-4-amine compounds.

Synthesis and properties of 2′-O,4′-C-spirocyclopropylene bridged nucleic acid (scpBNA), an analogue of 2′,4′-BNA/LNA bearing a cyclopropane ring

2′-O,4′-C-Spirocyclopropylene bridged nucleic acid (scpBNA), an analogue of 2′-O,4′-C-methylene bridged nucleic acid (2′,4′-BNA/LNA) bearing a cyclopropane ring at the 6′-position, was synthesized and successfully incorporated into oligonucleotides. The s

4'-Difluoromethyl Substituted Nucleoside Derivatives as Inhibitors of Influenza RNA Replication

The application discloses nucleoside derivatives of Formula I as inhibitors of Influenza RNA replication. In particular, the application discloses the use of purine and pyrimidine nucleoside derivatives of Formula I as inhibitors of Influenza RNA replication and pharmaceutical compositions containing such compounds.

Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

The synthesis of 2′-O,4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation-Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl- and 5′-C-methyl-modified bicyclic guanosines were evaluated, along with the known uracil-, cytosine-, adenine-, guanine-LNA and guanine-ENA nucleosides, as potential antiviral agents and found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay. Examination of the corresponding nucleoside triphosphates, however, against the purified HCV NS5B polymerase indicated that LNA-G and 2′-C-methyl-LNA-G are potent inhibitors of both 1b wild type and S282T mutant enzymes in vitro. Activity was further demonstrated for the LNA-G-triphosphate against HCV NS5B polymerase genotypes 1a, 2a, 3a and 4a. A phosphorylation by-pass prodrug strategy may be required to promote anti-HCV activity in the replicon assay.

BRIDGED ARTIFICIAL NUCLEOSIDE AND NUCLEOTIDE

It is an object of the present invention to provide a novel molecule for antisense therapies which is not susceptible to nuclease degradation in vivo and has a high binding affinity and specificity for the target mRNAs and which can efficiently regulate expression of specific genes. The novel artificial nucleoside of the present invention has an amide bond introduced into a bridge structure of 2′,4′-BNA/LNA. The oligonucleotide containing the 2′,4′-bridged artificial nucleotide has a binding affinity for a single-stranded RNA comparable to known 2′,4′-BNA/LNA and has an increased nuclease resistance over LNA. Particularly, it is expected to be applied to nucleic acid drugs because of its much stronger binding affinity for single-stranded RNAs than S-oligo's affinity

Fine tuning of electrostatics around the internucleotidic phosphate through incorporation of modified 2′,4′-carbocyclic-LNAs and -ENAs leads to significant modulation of antisense properties

(Chemical Equation Presented) In the antisense (AS) and RNA interference (RNAi) technologies, the native single-stranded 2′-deoxyoligonucleotides (for AS) or double-stranded RNA (for RNAi) are chemically modified to bind to the target RNA in order to give improved downregulation of gene expression through inhibition of RNA translation. It is shown here how the fine adjustment of the electrostatic interaction by alteration of the substituents as well as their stereochemical environment around the internucleotidic phosphodiester moiety near the edge of the minor grove of the antisense oligonucleotides (AON)-RNA heteroduplex can lead to the modulation of the antisense properties. This was demonstrated through the synthesis of various modified carbocyclic-locked nucleic acids (LNAs) and -ethylene-bridged nucleic acids (ENAs) with hydroxyl and/or methyl substituents attached at the carbocyclic part and their integration into AONs by solid-phase DNA synthesis. The target affinity toward the complementary RNA and DNA, nuclease resistance, and RNase H elicitation by these modified AONs showed that both the nature of the modification (-OH versus -CH3) and their respective stereochemical orientations vis-à-vis vicinal phosphate play a very important role in modulating the AON properties. Whereas the affinity to the target RNA and the enzymatic stability of AONs were not favored by the hydrophobic and sterically bulky modifications in the center of the minor groove, their positioning at the edge of the minor groove near the phosphate linkage resulted in significantly improved nuclease resistance without loss of target affinity. On the other hand, hydrophilic modification, such as a hydroxyl group, close to the phosphate linkage made the internucleotidic phosphodiester especially nucleolytically unstable, and hence was not recommended. The substitutions on the carbocyclic moiety of the carba-LNA and -ENA did not affect significantly the choice of the cleavage sites of RNase H mediated RNA cleavage in the AON/RNA hybrid duplex, but the cleavage rate depended on the modification site in the AON sequence. If the original preferred cleavage site by RNase H was included in the 4-5nt stretch from the 3′-end of the modification site in the AON, decreased cleavage rate was observed. Upon screening of 52 modified AONs, containing 13 differently modified derivatives at C6′ and C7′ (or C8′) of the carba-LNAs and -ENAs, two excellent modifications in the carba-LNA series were identified, which synergistically gave outstanding antisense properties such as the target RNA affinity, nuclease resistance, and RNase H activity and were deemed to be ideal candidates as potential antisense or siRNA therapeutic agents.

FIVE- AND SIX-MEMBERED CONFORMATIONALLY LOCKED 2',4'- CARBOCYCLIC RIBO-THYMIDINES FOR THE TREATMENT OF INFECTIONS AND CANCER

Compounds (1, 2, 3, 4) according to the formulae shown below: (Formula 1, 2, 3,4). For General Formula1-4:N=1-Thyminyl,9-Adeninyl,9-Guaninyl,1-Cytosinyl, 5-methyl-1-cytosinyl, 5-trifluoromethyl-1-cytosinyl, 5-fluoro-1-cytosinyl, 5-fluoro-1-cytosinyl, 5-tr

Five- and six-membered conformationally locked 2′,4′- carbocyclic ribo-thymidines: Synthesis, structure, and biochemical studies

Two unusual reactions involving the 5-hexenyl or the 6-heptenyl radical cyclization of a distant double bond at C4′ and the radical center at C2′ of the ribofuranose ring of thymidine have been used as key steps to synthesize North-type conformationally c