20397-91-5

Upstream product

• 613-90-1 benzoyl cyanide 
• 16535-78-7 1-(β-D-xylofuranosyl)uracil 
• 58-96-8 1-(β-L-arabinofuranosyl)-uracil 
• 120019-54-7 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-arabinofuranoside 
• 66-22-8 uracil 
• 3080-30-6 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose 
• 532-32-1 sodium benzoate 
• 259856-99-0 1-(β-L-arabinofuranosyl-2-O-methanesulfonyl-3,5-di-O-benzoyl)uracil 
• 171866-28-7 1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose 
• 31615-98-2 1-(3,5-Di-O-benzoyl-β-L-arabinofuranosyl)uracil 
• 31615-96-0 3',5'-di-O-benzoyl-2,2'-anhydro-L-uridine 
• 31501-46-9 (2S,3S,3aR,9aS)-3-hydroxy-2-(hydroxymethyl)-2,3,3a,9a-tetrahydro-6H-furo[2,3’:4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 35939-60-7 2-amino-β-L-arabinofurano[1',2':4,5]oxazoline 
• 98-88-4 benzoyl chloride 

Downstream Products

• 68027-41-8 1-(2',3',5'-tri-O-benzoyl-β-D-xylofuranosyl)-5-fluorouracil 
• 1382804-43-4 C₃₄H₂₅ClN₂O₉S 
• 1382804-45-6 C₃₄H₂₅BrN₂O₉S 
• 1382804-47-8 C₃₄H₂₅IN₂O₉S 
• 1382804-54-7 C₃₀H₂₄IN₃O₈ 
• 1382804-56-9 C₃₄H₂₇N₃O₈S 
• 1382804-58-1 C₃₄H₂₆ClN₃O₈S 
• 1382804-60-5 C₃₄H₂₆BrN₃O₈S 
• 1382804-62-7 C₃₄H₂₆IN₃O₈S 
• 1382804-38-7 C₃₀H₂₃ClN₂O₉ 
• 1382804-40-1 C₃₀H₂₃BrN₂O₉ 
• 552827-64-2 C₃₀H₂₃IN₂O₉ 
• 1382804-41-2 C₃₄H₂₆N₂O₉S 
• 58-96-8 L-uridine 

Relevant academic research and scientific papers

MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF

The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

Synthesis and cytotoxic activity of novel 5-substituted-1-(β-L- arabinofuranosyl) pyrimidine nucleosides

A series of new 5-halogeno-1-(β-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)- ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 μM concentrations. Copyright Taylor and Francis Group, LLC.

An economical synthesis of D- and L-pyrimidine arabinoand ribonucleosides

The one-step synthesis of several β-D/L-arabino- and ribonucleosides was performed in good yields under reflux or microwave-assisted fusion method. A comparison of the two methods showed that better yields were obtained using the reflux conditions. Copyright Taylor and Francis Group, LLC.

A procedure for facile synthesis of nucleosides using N, O-Bistrimethyl- silylacetamide in the presence of natural phosphate coated with potassium iodide

Several α-D/L-arabino and β-D/L- xylonucleosides were synthesized in good yields under mild conditions by N-glycosylation of 1-O-acetyl D/L- arabino, and xylofuranose, with silylated nucleobases (uracil, thymine and 6- azauracil) in acetonitrile using natural phosphate (NP) coated with potassium iodide in BSA as catalyst.

Stereocontrolled Syntheses of Deoxyribonucleosides via Photoinduced Electron-Transfer Deoxygenation of Benzoyl-Protected Ribo- and Arabinonucleosides

The stereocontrolled, de novo syntheses of β-2′-deoxy-, α-2′-deoxy-, β-3′-deoxy-, and β-2′,3′-dideoxyribonucleosides are described. Strategically protected ribose, arabinose, and xylose glycosylation precursors were synthesized bearing C2-esters capable of directing Vorbrueggen glycosylation. The key step is the regioselective deoxygenation of the desired hydroxyl group as either the benzoyl- or 3-(trifluoromethyl)benzoyl derivative. This deoxygenation is accomplished via a photoinduced electron-transfer (PET) mechanism using carbazole derivatives as the photosensitizer. The syntheses of the desired deoxynucleoside generally proceed in three steps from a common, readily available precursor.

Enantioselective synthesis and biological evaluation of 5-o-carboranyl pyrimidine nucleosides

Base-modified carborane-containing nucleosides such as 5-o-carboranyl-2'-deoxyuridine (CDU) when combined with neutrons have potential for the treatment of certain malignancies. Lack of toxicity in various cells, high accumulation in cancer cells and intracellular phosphorylation are desirable characteristics for modified nucleosides used in boron neutron capture therapy (BNCT) for brain tumors and other malignancies. The aim of this work was to synthesize the two β-enantiomers of several 5-o-carboranyl-containing nucleosides. These derivatives may possess favorable properties such as high lipophilicity, high transportability, the ability to be phosphorylated, and resistance to catabolism. β-Isomers of 2',3'-dihydroxynucleosides and analogues containing a heteroatom in the sugar moiety were also synthesized. Carboranyl pyrimidine nucleosides were prepared either from the parent β-D-nucleoside, β-L-nucleoside, or by a coupling reaction. The dioxolane derivative 7Scheme 1Reagents and conditions: (a) 1,1,1,3,3,3-hexamethydisilazane, ammonium sulfate, reflux, 6 h; (b) tin(IV) chloride, CH2Cl2, 0°C, 2h; (c) tetrabutylammonium fluoride, 1 M sol in THF, 0°C, 3h. was prepared by a coupling reaction between protected 5-o-carboranyluracil (8, CU) and the corresponding protected heterocycle. Specific catalysts were used during the N-glycosylation process to favor the formation of the β-isomer. Biological evaluation of these new chiral 5-o-carboranyl pyrimidine derivatives indicated that most of these compounds have low toxicity in a variety of normal and malignant cells and achieved high cellular levels in a lymphoblastoid cell line. Increasing the number of hydroxyl groups on the sugar moiety decreased the cellular accumulation and serum binding to different extents. Five compounds were identified for further biological evaluation as potential agents for BNCT. Copyright (C) 1999 Elsevier Science Ltd.

Improvements in the synthesis of L-ribonucleosides for the preparation of mirror-image oligoribonucleotides

Different improvements are described for the chemical synthesis of L- ribonucleosides corresponding to the four natural bases. These nucleosides properly protected were used to synthesize successfully a 27-base long L- oligoribonucleotide.

L-Ribonucleosides from L-xylose

L-Xylose was converted into a L-ribose derivative via an oxidation/reduction procedure. The L-ribosyl donor was submitted to a glycosidation reaction according to Vorbruggen's conditions to give L- ribonucleosides (L-uridine, L-cytidine, L-adenosine and L-guanosine) in high yield.

L-ribonucileosides for racemic RNA

Two L-ribosyl donors were synthesised from L-xylose, then submitted to a glycosidation reaction according to Vorbruggen's conditions to furnish L- ribonucleosides in high yield.

Chirally-modified oligonucleotides and the control of gene expression. The case of L-DNAs and -RNAs

The affinity of L-DNAs, L-RNAs and LD-DNAs for homopurine · homopyrimidine d.s. D-DNA and s.s. D-RNA was probed by gel electrophoresis and CD spectroscopy. It was found that the L-modified oligomers do not bind to d.s. DNA and to natural RNA that contains all four natural bases. Thus they cannot be used, in general, for the control of gene expression according to the antigene and antisense methodologies. Heterochiral complexes with 1:1 stoichiometry and low hem stability are formed, instead, by homopurinic L- RNA or L/D-DNA and homopyrimidinic L-RNA with the W/C complementary natural RNA sequences.