96291-75-7

Usage

Uses

Used in Organic Synthesis:
1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose is used as a building block in organic synthesis for the preparation of other complex molecules. Its unique structure and properties make it a versatile component in the synthesis of various organic compounds.
Used in Carbohydrate Chemistry Research:
1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose is used as a research tool in the field of carbohydrate chemistry. Its structure and properties allow scientists to study the behavior and interactions of carbohydrates, contributing to a deeper understanding of their role in biological systems.
Used in Medicinal Chemistry:
1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose is used as a potential drug target in medicinal chemistry. Its unique structure and properties make it a promising candidate for the development of new therapeutic agents, particularly in the areas of drug discovery and design.
Used in Pharmaceutical Industry:
1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique properties and reactivity make it a valuable component in the development of new drugs and drug delivery systems.
Used in Biochemical Research:
1,3,5-Tri-O-acetyl-2-deoxy-beta-D-erythro-pentofuranose is used as a research tool in biochemical studies. Its structure and properties allow researchers to investigate the role of carbohydrates in various biological processes, such as cell signaling, immune response, and molecular recognition.

InChI:InChI=1/C11H16O7/c1-6(12)15-5-10-9(16-7(2)13)4-11(18-10)17-8(3)14/h9-11H,4-5H2,1-3H3/t9-,10+,11+/m0/s1

Upstream product

• 533-67-5 2-Deoxy-D-ribose 
• 108-24-7 acetic anhydride 
• 36792-88-8 2-deoxy-D-ribose 
• 452-51-7 D-2-deoxyribose 
• 151767-35-0 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside 
• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 

Downstream Products

• 479582-36-0 1-hydroxy-2-(3',5'-di-O-acetyl-2'-deoxy-β-D-ribofuranosyl)benzene 
• 1254186-96-3 1-(3,5-di-O-acetyl-2-deoxy-D-ribofuranosyl)-5-azacytosine 
• 22432-93-5 4-amino-1-(O³,O⁵-diacetyl-β-D-erythro-2-deoxy-pentofuranosyl)-1H-[1,3,5]triazin-2-one 
• 50-89-5 thymidine 
• 7481-90-5 3',4'-anhydrothymidine 
• 3056-17-5 stavudin 
• 6979-97-1 3',5'-diacetylthymidine 
• 22432-93-5 3',5'-O-acetyl-2'-deoxy-5-azacytidine 
• 22969-05-7 1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-2-one 
• 1402737-97-6 p-tolyl-3,5-di-O-acetyl-1-thio-2-deoxy-α-D-ribofuranoside 
• 1402737-50-1 p-tolyl-3,5-di-O-acetyl-1-thio-2-deoxy-β-D-ribofuranoside 
• 367518-79-4 C₅₅H₆₆N₇O₁₇PSi 
• 367518-81-8 6-[2’-deoxy-3’-O-dimethoxytrityl-α-D-ribofuranose-1’-yl]amino-5-nitro-2-(phenoxylacetyl)amino-3H-pyrimidine-4-one 

Relevant academic research and scientific papers

SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG

The invention is a drug for anticancer and antiviral therapy, comprising a nucleoside analogue (7) comprising a furan ring irreversibly bound to the RNA/DNA synthesis chain by phosphodiester bonds and having SP3 hybridization, and folic acid (A) bound to the nucleoside analogue (7) comprising furan ring. The synthesis method of the said nucleoside analogue is also contained within the scope of the invention. In this work, a nucleoside-analogue was transformed after converting the furan-ring hybridization from Sp2 to Sp3 to make it more selectivity with different enzymes and linking it via site 5 with the effective folic acid towards entering the substances inside the cells and to become the final compound possessing anti-cancer and anti- virus properties after controlling the replication and reproduction process in DNA.

Method for synthesizing decitabine key intermediate by solid acid catalysis

The invention belongs to the technical field of medicinal chemistry, and relates to a method for synthesizing a decitabine key intermediate (formula II) by solid acid catalysis. The method is characterized in that silicon dioxide loaded stannic chloride (SnCl4) is used as a catalyst for glycosylation reaction. The method has the advantages that the problem of complicated post treatment of a liquidacid catalyst is solved, and the content of beta-configuration intermediate can be effectively improved.

First characterisation of two important postulated intermediates in the formation of a HydT DNA lesion, a thymidine oxidation product

A number of environmental pollutants and endogenous oxidation agents form 1-(2-deoxy-β-d-ribofuranosyl)-5-hydroxy-5-methylhydantoin (HydT), an important DNA lesion resulting from thymidine oxidation. In this paper, two intermediates, postulated in the formation of HydT, have been characterised for the first time. The first, N1-formyl-N3-pyruvoylurea intermediate, was produced by the ozonolysis reaction of 2′,3′,5′-tri-O-acetylribo-, 3′,5′-di-O-TBS- and N3,O3′,O5-tribenzyl-protected thymidines and was shown to produce, upon decomposition and depending on the protecting group and the conditions, HydT alone, or together with protected-β-d-ribofuranosyl-N1-formylurea and formamide products. In addition, the second and long sought, open-chain-pyruvoylurea intermediate, was produced through de novo synthesis in protected β-d-ribofuranosyl-, 2-deoxy-β-d-ribofuranosyl- and 2-deoxy-β-d-ribopyranosyl systems. The conditions that induce the cyclization to the hydantoin ring of HydT have been determined. The chemistry utilised in the de novo synthesis is suitable for generating isotopically labelled HydT, as a reference in isotope-dilution-aided quantification of DNA damage.

Synthesis of 2-deoxy ribose related disaccharide nucleoside and its phosphoramidite

Synthesis of impurity reference compound of anti-tumor drug ISIS 183750 was achieved. In this process, a general method for synthesis of 2-deoxy ribosyl disaccharide nucleosides was established for the first time.

Sono-transition-metal catalysis of one-pot three-step synthesis of glycosyl-1,2,3-triazoles

As a continuation of our studies directed at the development of straightforward and sustainable methodologies, we describe herein an original example of a combined effect of ultrasonic activation and iron-copper dual catalysis that allows an efficient and ecofriendly one-pot, three-step route to a new series of nucleoside-substituted triazoles. The reactions were carried out under both conventional and ultrasonic irradiation conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Synthesis and calcium mobilization activity of cADPR analogues which integrate nucleobase, northern and southern ribose modifications

Novel cADPR mimics, which integrate nucleobase, northern and southern ribose modifications were synthesized. The key steps of the synthesis were a Cu(I)-catalyzed Hueisgen [3+2] cycloaddition and a microwave-assisted intramolecular pyrophosphorylation. Preliminary biological investigations showed that these cADPR mimics are membrane-permeating agonists of the calcium signaling pathway. The introduction of chlorine or fluorine at the 2'-position of the southern riboses led to a decrease of activity. The existence of a hydrophobic group on the 3'-OH of the southern riboses does not obviously alter the agonistic activity.

Ultrasound-assisted one-pot synthesis of anti-CML nucleosides featuring 1,2,3-triazole nucleobase under iron-copper catalysis

A simple and efficient synthesis of modified 1,2,3-triazole nucleosides was developed. The strategy involved sequential one-pot acetylation-azidation- cycloaddition procedure and was found to be highly effective under a cooperative effect of ultrasound activation and iron/copper catalysis. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions. This one-pot procedure provides several advantages such as operational simplicity, high yield, safety and environment friendly protocol. The resulting substituted nucleosides were evaluated for their anticancer activity against K562 chronic myelogenous leukemia (CML) cell line.

PROCESS FOR THE PREPARATION OF (2R.3S)-2-(HYDROXYMETHYL) -5-METHOXYTETRAHYDROFURAN-3-OL AND ACETYLATED DERIVATIVES THEREOF, FREE OF PYRANOSE COMPOUNDS

A method of preparing a ribofuranose derivative essentially free of pyranose compounds includes a step of contacting a solution of MDR containing MDRP as an impurity in a solvent including methanol and/or tetrahydrofuran with at least one alkali metal periodate under conditions sufficient to oxidize at least a portion of the MDRP. MDR containing at most 5 wt% of MDRP based on the total weight of MDR and MDRP may be produced.

An atom-efficient and powerful method for direct esterification of silyl ethers catalyzed by HClO4-SiO2

An efficient and convenient procedure for direct esterification of alkyl and aryl silyl ethers with Ac2O and a catalyst system of perchloric acid immobilized on a silica gel (HClO4-SiO2) has been developed. The silyl protecting groups are directly replaced by acetyls and the protecting groups themselves are transformed into acetates as the sole byproducts, which can be readily recovered and converted back to silylchlorides, the original protecting agents, thus minimizing wastes.

Peracetylated β-allyl C-glycosides of D-ribofuranose and 2-deoxy-D-ribofuranose in the chemical literature: Until now, mirages in the literature

The peracetylated β-allyl C-glycosides of D-ribofuranose (8) and 2-deoxy-D-ribofuranose (13) were stereoselectively prepared via the isopropylidene derivatives 3 and 4. These reactions represent what are, to the best of our knowledge, the first preparation of these apparently simple derivatives whose structures were carefully proved by NMR and X-ray investigations. Publications which allegedly described the synthesis of 8 and 13 were critically examined. Georg Thieme Verlag Stuttgart.